BE572947A - - Google Patents

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Publication number

BE572947A

BE572947A BE572947DA BE572947A BE 572947 A BE572947 A BE 572947A BE 572947D A BE572947D A BE 572947DA BE 572947 A BE572947 A BE 572947A

Authority

BE

Belgium

Prior art keywords

alpha

phenyl

acid

chloride

sodium

Prior art date

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• -1 dialkylaminoalkyl chloride Chemical compound 0.000 claims description 15
• FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 12
• 150000001875 compounds Chemical class 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 238000010992 reflux Methods 0.000 claims description 6
• 150000001261 hydroxy acids Chemical class 0.000 claims description 5
• 150000002148 esters Chemical class 0.000 claims description 4
• 229910000033 sodium borohydride Inorganic materials 0.000 claims description 4
• YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Substances [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 claims description 4
• ODGROJYWQXFQOZ-UHFFFAOYSA-N sodium;boron(1-) Chemical compound [B-].[Na+] ODGROJYWQXFQOZ-UHFFFAOYSA-N 0.000 claims description 4
• ISSYFABJJSOCQG-UHFFFAOYSA-N 3-hydroxy-2-methyl-2-phenylpropanoic acid Chemical compound OCC(C)(C(O)=O)C1=CC=CC=C1 ISSYFABJJSOCQG-UHFFFAOYSA-N 0.000 claims description 3
• 125000002252 acyl group Chemical group 0.000 claims description 3
• VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
• 125000004432 carbon atoms Chemical group C* 0.000 claims description 2
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
• 229910052739 hydrogen Inorganic materials 0.000 claims description 2
• 239000001257 hydrogen Substances 0.000 claims description 2
• 238000005984 hydrogenation reaction Methods 0.000 claims description 2
• 159000000000 sodium salts Chemical class 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims 2
• 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
• 238000006460 hydrolysis reaction Methods 0.000 claims 1
• VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
• RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
• 239000000203 mixture Substances 0.000 description 21
• 239000000243 solution Substances 0.000 description 18
• 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 15
• KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
• HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
• 230000002378 acidificating Effects 0.000 description 9
• 229910052708 sodium Inorganic materials 0.000 description 8
• 239000011734 sodium Substances 0.000 description 8
• FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
• 239000002253 acid Substances 0.000 description 7
• KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
• IQFVPQOLBLOTPF-HKXUKFGYSA-L Congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 5
• 239000012259 ether extract Substances 0.000 description 5
• 238000003306 harvesting Methods 0.000 description 5
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
• YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-N,N-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
• 238000006243 chemical reaction Methods 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 239000000284 extract Substances 0.000 description 4
• 239000000706 filtrate Substances 0.000 description 4
• 238000002844 melting Methods 0.000 description 4
• 239000002244 precipitate Substances 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• 239000011780 sodium chloride Substances 0.000 description 4
• 235000011121 sodium hydroxide Nutrition 0.000 description 4
• 239000002904 solvent Substances 0.000 description 4
• 241000700159 Rattus Species 0.000 description 3
• 238000001990 intravenous administration Methods 0.000 description 3
• PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
• 229910052938 sodium sulfate Inorganic materials 0.000 description 3
• 235000011152 sodium sulphate Nutrition 0.000 description 3
• 238000003756 stirring Methods 0.000 description 3
• GJXTXPRZKRDQLG-UHFFFAOYSA-N 2-(hydroxymethyl)-2-phenylbutanoic acid Chemical compound CCC(CO)(C(O)=O)C1=CC=CC=C1 GJXTXPRZKRDQLG-UHFFFAOYSA-N 0.000 description 2
• 241000283973 Oryctolagus cuniculus Species 0.000 description 2
• 239000007864 aqueous solution Substances 0.000 description 2
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
• OFOBLEOULBTSOW-UHFFFAOYSA-N malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
• 239000003208 petroleum Substances 0.000 description 2
• 235000017557 sodium bicarbonate Nutrition 0.000 description 2
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
• CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
• 239000002699 waste material Substances 0.000 description 2
• QSISDJVWBRIWPT-UHFFFAOYSA-M 2-ethoxycarbonyl-4-phenylbutanoate Chemical compound CCOC(=O)C(C([O-])=O)CCC1=CC=CC=C1 QSISDJVWBRIWPT-UHFFFAOYSA-M 0.000 description 1
• VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
• 229930006677 A03BA01 - Atropine Natural products 0.000 description 1
• 229960004373 Acetylcholine Drugs 0.000 description 1
• RKUNBYITZUJHSG-SPUOUPEWSA-N Atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 1
• 229960000396 Atropine Drugs 0.000 description 1
• PASDCCFISLVPSO-UHFFFAOYSA-N Benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
• PBJDSFXEEYKQPJ-UHFFFAOYSA-N C(C)(=O)OCC(C(=O)O)(CC)C1=CC=CC=C1 Chemical compound C(C)(=O)OCC(C(=O)O)(CC)C1=CC=CC=C1 PBJDSFXEEYKQPJ-UHFFFAOYSA-N 0.000 description 1
• 241000282472 Canis lupus familiaris Species 0.000 description 1
• 210000003405 Ileum Anatomy 0.000 description 1
• 241001465754 Metazoa Species 0.000 description 1
• 229960005439 Propantheline Bromide Drugs 0.000 description 1
• XLBIBBZXLMYSFF-UHFFFAOYSA-M Propantheline bromide Chemical compound [Br-].C1=CC=C2C(C(=O)OCC[N+](C)(C(C)C)C(C)C)C3=CC=CC=C3OC2=C1 XLBIBBZXLMYSFF-UHFFFAOYSA-M 0.000 description 1
• 208000005392 Spasm Diseases 0.000 description 1
• OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
• 150000001263 acyl chlorides Chemical class 0.000 description 1
• 125000004423 acyloxy group Chemical group 0.000 description 1
• 125000001931 aliphatic group Chemical group 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• FERIUCNNQQJTOY-UHFFFAOYSA-M butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
• 239000000812 cholinergic antagonist Substances 0.000 description 1
• 238000010908 decantation Methods 0.000 description 1
• 125000006202 diisopropylaminoethyl group Chemical group [H]C([H])([H])C([H])(N(C([H])([H])C([H])([H])*)C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 238000004821 distillation Methods 0.000 description 1
• COQGJBOHHFJYNC-UHFFFAOYSA-N ethyl 3-chloro-2-methyl-3-oxo-2-phenylpropanoate Chemical compound CCOC(=O)C(C)(C(Cl)=O)C1=CC=CC=C1 COQGJBOHHFJYNC-UHFFFAOYSA-N 0.000 description 1
• 230000002496 gastric Effects 0.000 description 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
• 239000005457 ice water Substances 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 230000000968 intestinal Effects 0.000 description 1
• 231100000636 lethal dose Toxicity 0.000 description 1
• 231100000053 low toxicity Toxicity 0.000 description 1
• 238000000034 method Methods 0.000 description 1
• 235000011837 pasties Nutrition 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 230000028327 secretion Effects 0.000 description 1
• 239000001187 sodium carbonate Substances 0.000 description 1
• 229910000029 sodium carbonate Inorganic materials 0.000 description 1
• 230000002048 spasmolytic Effects 0.000 description 1
• 239000006228 supernatant Substances 0.000 description 1