CH392508A - Procédé de préparation d'esters de 3-phényl-3-pyrrolidinols - Google Patents
Procédé de préparation d'esters de 3-phényl-3-pyrrolidinolsInfo
- Publication number
- CH392508A CH392508A CH7139059A CH7139059A CH392508A CH 392508 A CH392508 A CH 392508A CH 7139059 A CH7139059 A CH 7139059A CH 7139059 A CH7139059 A CH 7139059A CH 392508 A CH392508 A CH 392508A
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- ether
- solution
- mixture
- methyl
- Prior art date
Links
- 150000002148 esters Chemical class 0.000 title claims description 11
- AFQYBBFSDHKQJV-UHFFFAOYSA-N 3-phenylpyrrolidin-3-ol Chemical class C=1C=CC=CC=1C1(O)CCNC1 AFQYBBFSDHKQJV-UHFFFAOYSA-N 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 alkyl radical Chemical class 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000012458 free base Substances 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 86
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 36
- 239000000203 mixture Substances 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 22
- 238000010992 reflux Methods 0.000 description 21
- 239000000284 extract Substances 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 12
- 238000004821 distillation Methods 0.000 description 11
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 7
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- 239000002026 chloroform extract Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- CWLUFVAFWWNXJZ-UHFFFAOYSA-N 1-hydroxypyrrolidine Chemical class ON1CCCC1 CWLUFVAFWWNXJZ-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 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 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- VEUYRZJQDCCKKP-UHFFFAOYSA-N 1,2-dimethylpyrrolidin-3-one Chemical compound CC1N(C)CCC1=O VEUYRZJQDCCKKP-UHFFFAOYSA-N 0.000 description 3
- 150000004042 3-pyrrolidinones Chemical class 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- QGKLPGKXAVVPOJ-UHFFFAOYSA-N pyrrolidin-3-one Chemical compound O=C1CCNC1 QGKLPGKXAVVPOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- ZYPZDVCEBCVJGX-UHFFFAOYSA-N (1,4-dimethyl-3-phenylpyrrolidin-3-yl) propanoate Chemical compound C=1C=CC=CC=1C1(OC(=O)CC)CN(C)CC1C ZYPZDVCEBCVJGX-UHFFFAOYSA-N 0.000 description 2
- YKLWPXLYCBHVQQ-UHFFFAOYSA-N (4-methyl-3-phenylpyrrolidin-3-yl) acetate Chemical compound CC1C(CNC1)(OC(C)=O)C1=CC=CC=C1 YKLWPXLYCBHVQQ-UHFFFAOYSA-N 0.000 description 2
- BAYDLDJKTJEXLI-UHFFFAOYSA-N 1,2,4-trimethyl-3-phenylpyrrolidin-3-ol Chemical compound CN1C(C(C(C1)C)(O)C1=CC=CC=C1)C BAYDLDJKTJEXLI-UHFFFAOYSA-N 0.000 description 2
- OTRFAQOSMBFREC-UHFFFAOYSA-N 1,2-dimethyl-3-phenylpyrrolidin-3-ol Chemical compound CC1N(C)CCC1(O)C1=CC=CC=C1 OTRFAQOSMBFREC-UHFFFAOYSA-N 0.000 description 2
- XDFQFXXJLSXTQA-UHFFFAOYSA-N 1,4-dimethyl-3-phenylpyrrolidin-3-ol Chemical compound CC1CN(C)CC1(O)C1=CC=CC=C1 XDFQFXXJLSXTQA-UHFFFAOYSA-N 0.000 description 2
- GKVSNVPJRHQGOZ-UHFFFAOYSA-N 1,4-dimethylpyrrolidin-3-one Chemical compound CC1CN(C)CC1=O GKVSNVPJRHQGOZ-UHFFFAOYSA-N 0.000 description 2
- UQQSVHQSPTWCGS-UHFFFAOYSA-N 1,5-dimethyl-3-phenylpyrrolidin-3-ol Chemical compound C1N(C)C(C)CC1(O)C1=CC=CC=C1 UQQSVHQSPTWCGS-UHFFFAOYSA-N 0.000 description 2
- UIXHYJIVGSSLIS-UHFFFAOYSA-N 1-benzyl-4-methyl-3-phenylpyrrolidin-3-ol Chemical compound C(C1=CC=CC=C1)N1CC(C(C1)C)(O)C1=CC=CC=C1 UIXHYJIVGSSLIS-UHFFFAOYSA-N 0.000 description 2
- KHKJEZHCAXTVGB-UHFFFAOYSA-N 1-methyl-3-phenylpyrrolidin-3-ol Chemical compound C1N(C)CCC1(O)C1=CC=CC=C1 KHKJEZHCAXTVGB-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 2
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 150000002902 organometallic compounds Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- RBBBYDOGRKOESS-UHFFFAOYSA-N (1,2-dimethyl-3-phenylpyrrolidin-3-yl) propanoate;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C1(OC(=O)CC)CCN(C)C1C RBBBYDOGRKOESS-UHFFFAOYSA-N 0.000 description 1
- ZBIWFRIPOVNKHR-UHFFFAOYSA-N (1,5-dimethyl-3-phenylpyrrolidin-3-yl) propanoate Chemical compound C=1C=CC=CC=1C1(OC(=O)CC)CC(C)N(C)C1 ZBIWFRIPOVNKHR-UHFFFAOYSA-N 0.000 description 1
- JPTMUTKSUNODEI-UHFFFAOYSA-N (1-benzyl-4-methyl-3-phenylpyrrolidin-3-yl) acetate Chemical compound C(C1=CC=CC=C1)N1CC(C(C1)C)(OC(C)=O)C1=CC=CC=C1 JPTMUTKSUNODEI-UHFFFAOYSA-N 0.000 description 1
- HSCOGTOYLILNHR-UHFFFAOYSA-N (1-methyl-3-phenylpyrrolidin-3-yl) propanoate Chemical compound C=1C=CC=CC=1C1(OC(=O)CC)CCN(C)C1 HSCOGTOYLILNHR-UHFFFAOYSA-N 0.000 description 1
- LWKBNDUQVZPXBZ-UHFFFAOYSA-N 1,2,4-trimethylpyrrolidin-3-one Chemical compound CC1CN(C)C(C)C1=O LWKBNDUQVZPXBZ-UHFFFAOYSA-N 0.000 description 1
- IVPWAPPZFLWSCL-UHFFFAOYSA-N 1,2-dimethylpyrrolidin-3-one hydrochloride Chemical compound Cl.CN1C(C(CC1)=O)C IVPWAPPZFLWSCL-UHFFFAOYSA-N 0.000 description 1
- WGNSIHQTQHENSN-UHFFFAOYSA-N 1,5-dimethylpyrrolidin-3-one Chemical compound CC1CC(=O)CN1C WGNSIHQTQHENSN-UHFFFAOYSA-N 0.000 description 1
- NSXHIJHCRCPVAS-UHFFFAOYSA-N 1-benzyl-4-methylpyrrolidin-3-one Chemical compound C1C(=O)C(C)CN1CC1=CC=CC=C1 NSXHIJHCRCPVAS-UHFFFAOYSA-N 0.000 description 1
- SLPUTJFVMJPMKV-UHFFFAOYSA-N 1-methylpyrrolidin-3-one Chemical compound CN1CCC(=O)C1 SLPUTJFVMJPMKV-UHFFFAOYSA-N 0.000 description 1
- UNIJBMUBHBAUET-UHFFFAOYSA-N 3-(methylamino)propanenitrile Chemical compound CNCCC#N UNIJBMUBHBAUET-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- DEMWVPJPBRRRLH-UHFFFAOYSA-N 4-amino-1,5-dimethyl-2,5-dihydropyrrole-3-carbonitrile Chemical compound CC1N(C)CC(C#N)=C1N DEMWVPJPBRRRLH-UHFFFAOYSA-N 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- JILWMMGUDYSCKH-UHFFFAOYSA-N Cl.CN1CC(C(C1)C)=O Chemical compound Cl.CN1CC(C(C1)C)=O JILWMMGUDYSCKH-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940067621 aminobutyrate Drugs 0.000 description 1
- 125000005219 aminonitrile group Chemical group 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- QAWBXZYPFCFQLA-UHFFFAOYSA-N butanoyl bromide Chemical compound CCCC(Br)=O QAWBXZYPFCFQLA-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical compound CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- NCHRVWIOGHJADK-UHFFFAOYSA-N methyl 4-(methylamino)butanoate Chemical compound CNCCCC(=O)OC NCHRVWIOGHJADK-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000020075 ouzo Nutrition 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- LUKSBMJXPCFBKO-UHFFFAOYSA-N prodilidine Chemical compound C=1C=CC=CC=1C1(OC(=O)CC)CCN(C)C1C LUKSBMJXPCFBKO-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- KSMWLICLECSXMI-UHFFFAOYSA-N sodium;benzene Chemical compound [Na+].C1=CC=[C-]C=C1 KSMWLICLECSXMI-UHFFFAOYSA-N 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB10617/58A GB862513A (en) | 1958-04-02 | 1958-04-02 | Pyrrolidine compounds and methods for producing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH392508A true CH392508A (fr) | 1965-05-31 |
Family
ID=9971170
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH7139059A CH392508A (fr) | 1958-04-02 | 1959-03-31 | Procédé de préparation d'esters de 3-phényl-3-pyrrolidinols |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3256297A (en, 2012) |
| CH (1) | CH392508A (en, 2012) |
| DE (2) | DE1176144B (en, 2012) |
| ES (1) | ES247911A1 (en, 2012) |
| FR (2) | FR1374302A (en, 2012) |
| GB (1) | GB862513A (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3185702A (en) * | 1959-03-16 | 1965-05-25 | Lunsford Carl Dalton | Basic esters of 3-aryl-3-pyrrolidinols |
| US3462452A (en) * | 1966-05-17 | 1969-08-19 | Parke Davis & Co | 1-phenethyl or p-aminophenethyl-3-(m-hydroxy- or alkanoyloxy-phenyl)-3-propylpyrrolidines and salts thereof |
| US4774340A (en) * | 1984-04-06 | 1988-09-27 | Miles Inc. | Method for preparing 3-hydroxy pyrroles and esters thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2878264A (en) * | 1959-03-17 | Substituted amino alcohols | ||
| US2880211A (en) * | 1959-03-31 | Chcoochj | ||
| US2850500A (en) * | 1958-09-02 | Chjchzcoochj | ||
| US2824875A (en) * | 1958-02-25 | Certificate of correction | ||
| GB483258A (en) * | 1936-06-08 | 1938-04-14 | Arthur George Bloxam | Manufacture of basic esters of polyarylacetic acids |
| GB629196A (en) * | 1946-07-08 | 1949-09-14 | Roche Products Ltd | Piperidine derivatives |
| NL94071C (en, 2012) * | 1954-04-20 | |||
| US2765314A (en) * | 1954-05-12 | 1956-10-02 | Rohm & Haas | Preparation of esters |
| US2784192A (en) * | 1954-06-24 | 1957-03-05 | Rohm & Haas | Preparation of 4-hydroxypiperidines |
| US2846437A (en) * | 1955-09-12 | 1958-08-05 | Sterling Drug Inc | Lower alkyl 4-phenyl-1-(substituted-alkyl) piperidine-4-carboxylates and preparationthereof |
-
1958
- 1958-04-02 GB GB10617/58A patent/GB862513A/en not_active Expired
-
1959
- 1959-03-14 ES ES0247911A patent/ES247911A1/es not_active Expired
- 1959-03-20 US US800643A patent/US3256297A/en not_active Expired - Lifetime
- 1959-03-31 CH CH7139059A patent/CH392508A/fr unknown
- 1959-03-31 FR FR790838A patent/FR1374302A/fr not_active Expired
- 1959-04-01 DE DEP22513A patent/DE1176144B/de active Pending
- 1959-04-01 DE DEP26856A patent/DE1241829B/de active Pending
-
1960
- 1960-08-31 FR FR837391A patent/FR594M/fr active Active
Also Published As
| Publication number | Publication date |
|---|---|
| GB862513A (en) | 1961-03-08 |
| FR594M (en, 2012) | 1961-06-12 |
| US3256297A (en) | 1966-06-14 |
| FR1374302A (fr) | 1964-10-09 |
| ES247911A1 (es) | 1959-08-16 |
| DE1241829B (de) | 1967-06-08 |
| DE1176144B (de) | 1964-08-20 |
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