GB560568A - Manufacture of basic 1 : 3-dialkoxy-propanols and 1 : 3-dialkoxy-propanones - Google Patents
Manufacture of basic 1 : 3-dialkoxy-propanols and 1 : 3-dialkoxy-propanonesInfo
- Publication number
- GB560568A GB560568A GB12440/41A GB1244041A GB560568A GB 560568 A GB560568 A GB 560568A GB 12440/41 A GB12440/41 A GB 12440/41A GB 1244041 A GB1244041 A GB 1244041A GB 560568 A GB560568 A GB 560568A
- Authority
- GB
- United Kingdom
- Prior art keywords
- propanol
- give
- methylphenoxy
- phenoxy
- reacted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- KKFDCBRMNNSAAW-UHFFFAOYSA-N 2-(morpholin-4-yl)ethanol Chemical compound OCCN1CCOCC1 KKFDCBRMNNSAAW-UHFFFAOYSA-N 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 2
- BPIIGTWIPYOEIV-UHFFFAOYSA-N 2-(diethylaminomethyl)-4-methylphenol Chemical compound CCN(CC)CC1=CC(C)=CC=C1O BPIIGTWIPYOEIV-UHFFFAOYSA-N 0.000 abstract 1
- KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 abstract 1
- QHPWRDNABXCTMP-UHFFFAOYSA-N 2-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NC(C)(C)O QHPWRDNABXCTMP-UHFFFAOYSA-N 0.000 abstract 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 abstract 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 229940117975 chromium trioxide Drugs 0.000 abstract 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- -1 methylisobutylamino- Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical class CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 125000001302 tertiary amino group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Basic 1 : 3-dialkoxy-propanols are prepared by reacting an epihydrin ether with an alcohol or a phenol there being present in the epihydrin ether or in the alcohol or phenol or in both at least one tertiary amino group. The propanols as prepared may be oxidized to the corresponding propanones. In examples (1) 2-Diethylaminomethyl-4-methyl phenol, prepared by the action of formaldehyde and diethylamine on para-cresol, is treated with epichlorhydrin in the presence of alcoholic sodium hydroxide to give 1-(b : g -epoxypropyloxy)-2-diethylaminomethyl-4-methylbenzene which on treatment with alcohol gives 1-(21-diethylaminomethyl-41 - methyl - phenoxy - 11 -) - 3 - ethoxy - propanol -2. In a similar manner there may be obtained the corresponding bases 1-(21-dimethylaminomethyl - 41 - methylphenoxy) - 3 - methoxy - propanol - 2, 1 - (21 - dimethylaminomethyl - 41 - methylphenoxy) - 3 - ethoxy - propanol - 2, 1 - (21 - piperidinomethyl - 41 - methylphenoxy) - 3 - methoxy - propanol - 2, 1 - (21 - piperidinomethyl - 41 - methylphenoxy)-3 - butyloxy - propanol - 2. (2) A mixture of epiphenylene and N-hydroxyethyl-piperidine is heated in an autoclave to give 1-phenoxy-3-N-piperidethoxypropanol-2. On oxidation with chromium trioxide in glacial acetic acid it is converted into the corresponding propanone. (3) Epiphenylene is heated with N-hydroxyethyl morpholine to give 1-phenoxy-3-morpholinylethoxy-propanol-2. (4) Epiguaiacoline is heated with diethylamino-ethanol to give 1-(21-methoxyphenoxy - 1) - 3 - diethylamino - ethoxypropanol-2. Other epiarylines and epialkylalkylines mentioned include epixylenyline o-, and p-epicresylines epiethylines, and epianyline. Other bases mentioned include methylpropylamino- or methylisopropylamino-ethanol, and methylisobutylamino-, or ethyl - tert. - butyl - amino-ethanol. (5) Epiphenylene and 2 : 3-dihydroxypropyl-1-diethylamine are reacted to give 1 - phenoxy - 3 - (31 - diethylamino - 21 - hydroxypropyloxy-1-g -propanol-2. (6) b -naphthol is reacted with epichlorhydrin in the presence of potassium hydroxide, and the epi-b -naphthyline so produced is reacted with triethanolamine to give 1-(b -naphthyloxy-3-dihydroxyethyl) - aminoethoxy - propanol - 2. (7) a -epinaphthalene is reacted with N-hydroxyethyl-morpholine to give 1-a -naphthyloxy-3-N-morpholinyl-ethoxypropanol-2. Specifications 546,286 and 555,192 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH560568X | 1910-09-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB560568A true GB560568A (en) | 1944-04-11 |
Family
ID=4520255
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB12440/41A Expired GB560568A (en) | 1910-09-26 | 1941-09-25 | Manufacture of basic 1 : 3-dialkoxy-propanols and 1 : 3-dialkoxy-propanones |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB560568A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2738351A (en) * | 1952-08-02 | 1956-03-13 | Bristol Lab Inc | Substituted glycerol ethers |
| US3228956A (en) * | 1962-11-14 | 1966-01-11 | Dow Chemical Co | Imidazoline derivatives of 2-propanols |
| WO1995011240A1 (en) * | 1993-10-22 | 1995-04-27 | Smithkline Beecham Plc | Amine derivatives as calcium channel antagonists |
-
1941
- 1941-09-25 GB GB12440/41A patent/GB560568A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2738351A (en) * | 1952-08-02 | 1956-03-13 | Bristol Lab Inc | Substituted glycerol ethers |
| US3228956A (en) * | 1962-11-14 | 1966-01-11 | Dow Chemical Co | Imidazoline derivatives of 2-propanols |
| WO1995011240A1 (en) * | 1993-10-22 | 1995-04-27 | Smithkline Beecham Plc | Amine derivatives as calcium channel antagonists |
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