CN101798271B - Method for preparing (+/-)-norepinephrine - Google Patents
Method for preparing (+/-)-norepinephrine Download PDFInfo
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- CN101798271B CN101798271B CN 201010124154 CN201010124154A CN101798271B CN 101798271 B CN101798271 B CN 101798271B CN 201010124154 CN201010124154 CN 201010124154 CN 201010124154 A CN201010124154 A CN 201010124154A CN 101798271 B CN101798271 B CN 101798271B
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- norepinephrine
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- SFLSHLFXELFNJZ-UHFFFAOYSA-N noradrenaline Chemical compound NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 title abstract description 13
- 238000000034 method Methods 0.000 title abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 13
- 239000000706 filtrate Substances 0.000 claims abstract description 10
- 230000001105 regulatory effect Effects 0.000 claims abstract description 10
- 238000001291 vacuum drying Methods 0.000 claims abstract description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 25
- 229960002748 norepinephrine Drugs 0.000 claims description 20
- CVXGFPPAIUELDV-UHFFFAOYSA-N phenacylazanium;chloride Chemical compound [Cl-].[NH3+]CC(=O)C1=CC=CC=C1 CVXGFPPAIUELDV-UHFFFAOYSA-N 0.000 claims description 10
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 238000003756 stirring Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000000047 product Substances 0.000 abstract description 8
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000003513 alkali Substances 0.000 abstract description 3
- 238000005576 amination reaction Methods 0.000 abstract description 3
- 239000006227 byproduct Substances 0.000 abstract description 3
- 239000003054 catalyst Substances 0.000 abstract description 3
- 238000001914 filtration Methods 0.000 abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 3
- 239000001257 hydrogen Substances 0.000 abstract description 3
- 239000012065 filter cake Substances 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 230000001276 controlling effect Effects 0.000 abstract 1
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YCIMNLLNPGFGHC-UHFFFAOYSA-N o-dihydroxy-benzene Natural products OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 3
- 210000001943 adrenal medulla Anatomy 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- -1 chloracetyl catechol Chemical compound 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 230000028327 secretion Effects 0.000 description 2
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 108060003345 Adrenergic Receptor Proteins 0.000 description 1
- 102000017910 Adrenergic receptor Human genes 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
Abstract
The invention discloses a method for preparing (+/-)-norepinephrine shown in a formula (II). The method comprises the following steps of: (a) adding water to dissolve 1-(3,4-dihydroxybenzene)-2-amino ethanone hydrochloride shown in a formula (I), shifting the obtained product into a hydrogenation bottle, adding a palladium-carbon catalyst, controlling reaction temperature to be between 10 and 45 DEG C, introducing hydrogen under normal pressure and performing reaction for 14 to 36 hours; and (b) filtering the obtained product after reaction is finished, regulating the pH of the obtained filtrate to be between 9 and 10 by using alkali, filtering the obtained product and performing vacuum drying on a filter cake to obtain the (+/-)-norepinephrine. In the method, an amination intermediate (1-(3,4-dihydroxybenzene)-2-amino ethanone hydrochloride) is used as a raw material, and the (+/-)-norepinephrine is obtained by introducing the hydrogen under normal pressure to perform reaction, so the method has the advantage of simple process, readily available raw material, low requirement on equipment, mild reaction conditions, implementation under normal pressure, high yield and purity of the product, few by-products, low production cost, suitability for industrial production and great application prospect.
Description
Technical field
The present invention relates to the field of chemical synthesis, the preparation method of especially a kind of (±)-norepinephrine.
Background technology
Norepinephrine (Norepinephrine), formal name used at school 1-(3,4-dihydroxyphenyl)-2-monoethanolamine is that suprarenin removes the material that forms behind the N-methyl, molecular formula C
8H
11O
3N, molecular weight 169.18, its structural formula is as follows:
Norepinephrine is a kind of neurotransmitter, and the mainly synthetic and secretion by adrenergic nerve tip in sympathetic postganglionic neuron and the brain is the main mediator that the latter discharges, and also is a kind of hormone, the synthetic and secretion by adrenal medulla, but content is less.Norepinephrine in the blood circulation is mainly from adrenal medulla.
Medicinal norepinephrine is a kind of adrenoceptor excitomotor, and the effect of vasoconstriction, rising blood pressure is arranged, and is mainly used in rescuing acute low mass formed by blood stasis and the caused shock of peripheral vasodilation etc.
Have opticity in the norepinephrine, the levo form curative effect is big 27 times than dextrorotatory form.Medicinal norepinephrine is mainly by synthetic.Traditional synthetic norepinephrine method is to generate the chloracetyl catechol under the heat with pyrocatechol and Mono Chloro Acetic Acid altogether in phosphorus oxychloride, obtain corresponding amination intermediate behind the aminolysis, obtain the racemize norepinephrine after the palladium carbon catalytic hydrogenation, split at last and obtain R-norepinephrine and S-norepinephrine.Method for hydrogenation commonly used need carry out pressure treatment to hydro genation system, to having relatively high expectations of hydrogenation equipment, also can produce more by product simultaneously, makes the purity drop of the finished product.
Summary of the invention
The objective of the invention is to overcome above-mentioned defective, a kind of method of low for equipment requirements, security good, product yield is high, purity is high preparation (±)-norepinephrine is provided, and products obtained therefrom (±)-norepinephrine can obtain R-norepinephrine and S-norepinephrine by fractionation.
A kind of preparation method suc as formula (±)-norepinephrine shown in (II) is characterized in that may further comprise the steps:
(a) will be dissolved in water suc as formula the amino acetophenone hydrochloride of the 1-shown in (I) (3,4-dihydroxyphenyl)-2-, and move into the hydrogenation bottle, and add palladium-carbon catalyst, the control temperature of reaction is 10～45 ℃, and normal pressure leads to hydrogen, reacts 14～36 hours;
(b) reaction finishes after-filtration, and it is 9～10 that gained filtrate is regulated the pH value with alkali, filters, and filter cake is carried out vacuum-drying, gets (±)-norepinephrine.
Further, described temperature of reaction is preferably 15～35 ℃.
Palladium content is 1%～15% in the described palladium-carbon catalyst, is preferably 3%～10%.
The described alkali of step (b) is a kind of in strong aqua, the NaOH aqueous solution, the KOH aqueous solution.
The present invention is raw material with amination intermediate (the amino acetophenone hydrochloride of 1-(3,4-dihydroxyphenyl)-2-), by logical H-H reaction under the normal pressure, makes (±)-norepinephrine, and this method is a kind of brand-new preparation method, and its technological process is easy, raw material is easy to get; Low for equipment requirements, the reaction conditions gentleness can be carried out under the normal pressure, and product yield height, purity height, by product are few, and production cost is low, is applicable to industrial production, has bigger application prospect.
Embodiment
Embodiment 1:
Add the amino acetophenone hydrochloride 203.5g of 1-(3,4-dihydroxyphenyl)-2-in the 2L reaction flask, water 770ml is heated to 55 ℃ under stirring, and moves in the 2L hydrogenation bottle, adds Pd/C (Pd:5%; Water: 63.7g 75%), temperature is 28 ℃ in the control, and the logical H-H reaction of normal pressure 18 hours is filtered.Filtrate being cooled to is lower than 10 ℃, adds strong aqua, and regulating the pH value is 9, filters, and vacuum-drying obtains solid 147.1g, and yield is that 87.0%, HPLC detects purity 99.3%.
Embodiment 2:
Add the amino acetophenone hydrochloride 203.5g of 1-(3,4-dihydroxyphenyl)-2-in the 2L reaction flask, water 770ml is heated to 55 ℃ under stirring, and moves in the 2L hydrogenation bottle, adds Pd/C (Pd:10%; Water: 35.1g 75%), temperature is 35 ℃ in the control, and the logical H-H reaction of normal pressure 28 hours is filtered.Filtrate being cooled to is lower than 10 ℃, adds strong aqua, and regulating the pH value is 9, filters, and vacuum-drying obtains solid 144.1g, and yield is that 85.3%, HPLC detects purity 99.1%.
Embodiment 3:
Add the amino acetophenone hydrochloride 203.5g of 1-(3,4-dihydroxyphenyl)-2-in the 2L reaction flask, water 770ml is heated to 55 ℃ under stirring, and moves in the 2L hydrogenation bottle, adds Pd/C (Pd:5%; Water: 55.6g 75%), temperature is 25 ℃ in the control, and the logical H-H reaction of normal pressure 20 hours is filtered.Filtrate being cooled to is lower than 10 ℃, adds strong aqua, and regulating the pH value is 10, filters, and vacuum-drying obtains solid 141.1g, and yield is that 83.5%, HPLC detects purity 98.5%.
Embodiment 4:
Add the amino acetophenone hydrochloride 203.5g of 1-(3,4-dihydroxyphenyl)-2-in the 2L reaction flask, water 770ml is heated to 55 ℃ under stirring, and moves in the 2L hydrogenation bottle, adds Pd/C (Pd:1%; Water: 163.7g 75%), temperature is 30 ℃ in the control, and the logical H-H reaction of normal pressure 34 hours is filtered.Filtrate being cooled to is lower than 10 ℃, adds strong aqua, and regulating the pH value is 10, filters, and vacuum-drying obtains solid 146.2g, and yield is that 86.5%, HPLC detects purity 99.2%.
Embodiment 5:
Add the amino acetophenone hydrochloride 203.5g of 1-(3,4-dihydroxyphenyl)-2-in the 2L reaction flask, water 770ml is heated to 55 ℃ under stirring, and moves in the 2L hydrogenation bottle, adds Pd/C (Pd:5%; Water: 50.2g 75%), temperature is 30 ℃ in the control, and the logical H-H reaction of normal pressure 48 hours is filtered.Filtrate being cooled to is lower than 10 ℃, adds strong aqua, and regulating the pH value is 9, filters, and vacuum-drying obtains solid 135.1g, and yield is that 80.0%, HPLC detects purity 99.6%.
Embodiment 6:
Add the amino acetophenone hydrochloride 203.5g of 1-(3,4-dihydroxyphenyl)-2-in the 2L reaction flask, water 770ml is heated to 55 ℃ under stirring, and moves in the 2L hydrogenation bottle, adds Pd/C (Pd:10%; Water: 43.2g 75%), temperature is 25 ℃ in the control, and the logical H-H reaction of normal pressure 22 hours is filtered.Filtrate being cooled to is lower than 10 ℃, adds strong aqua, and regulating the pH value is 9, filters, and vacuum-drying obtains solid 153.3g, and yield is that 90.7%, HPLC detects purity 99.4%.
Embodiment 7:
Add the amino acetophenone hydrochloride 203.5g of 1-(3,4-dihydroxyphenyl)-2-in the 2L reaction flask, water 770ml is heated to 55 ℃ under stirring, and moves in the 2L hydrogenation bottle, adds Pd/C (Pd:5%; Water: 70.2g 75%), temperature is 28 ℃ in the control, and the logical H-H reaction of normal pressure 28 hours is filtered.Filtrate being cooled to is lower than 10 ℃, adds strong aqua, and regulating the pH value is 10, filters, and vacuum-drying obtains solid 149.5g, and yield is that 88.5%, HPLC detects purity 99.6%.
Claims (1)
1. preparation method suc as formula (±)-norepinephrine shown in (II) is characterized in that may further comprise the steps:
Add the amino acetophenone hydrochloride 203.5g suc as formula the 1-shown in (I) (3,4-dihydroxyphenyl)-2-in the 2L reaction flask, water 770ml is heated to 55 ℃ under stirring, and moves in the 2L hydrogenation bottle, adds Pd/C 63.7g, wherein Pd:5%; Water: 75%; Temperature is 28 ℃ in the control, and the logical H-H reaction of normal pressure 18 hours is filtered; Filtrate being cooled to is lower than 10 ℃, adds strong aqua, and regulating the pH value is 9, filters, and vacuum-drying obtains (±)-norepinephrine solid 147.1g, and yield is that 87.0%, HPLC detects purity 99.3%;
（I） （II） 。
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010124154 CN101798271B (en) | 2010-03-15 | 2010-03-15 | Method for preparing (+/-)-norepinephrine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 201010124154 CN101798271B (en) | 2010-03-15 | 2010-03-15 | Method for preparing (+/-)-norepinephrine |
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| CN101798271A CN101798271A (en) | 2010-08-11 |
| CN101798271B true CN101798271B (en) | 2013-08-28 |
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| CN 201010124154 Active CN101798271B (en) | 2010-03-15 | 2010-03-15 | Method for preparing (+/-)-norepinephrine |
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Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013008247A1 (en) | 2011-07-13 | 2013-01-17 | Neon Laboratories Ltd. | Process for preparation of (dl) -norepinephrine acid addition salt, a key intermediate of (r) - (-) - norepinephrine |
| CN103435503B (en) * | 2013-09-02 | 2015-06-17 | 江苏宝众宝达药业有限公司 | Preparation process of phenylephrine key intermediate 3-hydroxyl-alpha-(methylamine ethyl)-phenylcarbinol (dextro-laevo isomer) |
| CN108107140A (en) * | 2017-12-19 | 2018-06-01 | 嘉实（湖南）医药科技有限公司 | The detection method of impurity in adrenaline intermediate |
| US10865180B2 (en) | 2018-08-10 | 2020-12-15 | Harman Finochem Limited | Process for the preparation of l-Norepinephrine bitartrate monohydrate having high enantiomeric purity |
| CN112225665A (en) * | 2020-10-28 | 2021-01-15 | 合肥亿帆生物制药有限公司 | Preparation method of noradrenaline bitartrate |
| CN114557990A (en) * | 2020-11-27 | 2022-05-31 | 山东大学 | Application of non-peptide compound in preparation of products for inhibiting coronavirus |
| CN113735720A (en) * | 2021-10-26 | 2021-12-03 | 成都倍特药业股份有限公司 | Method for preparing (+/-) -adrenaline |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1237574A (en) * | 1998-05-29 | 1999-12-08 | 中国科学院成都有机化学研究所 | Method for synthesizing phynylethanolamine compound |
-
2010
- 2010-03-15 CN CN 201010124154 patent/CN101798271B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1237574A (en) * | 1998-05-29 | 1999-12-08 | 中国科学院成都有机化学研究所 | Method for synthesizing phynylethanolamine compound |
Non-Patent Citations (1)
| Title |
|---|
| Adrian Weisz,et al..SYNTHESIS OF D/L-NOREPINEPHRINE- (PHENYL-U-13C.《Journal of Labelled Compounds and Radiopharmaceuticals》.1988,第XXV卷(第1期),第103-109页. * |
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| CN101798271A (en) | 2010-08-11 |
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