DE1445518A1 - Verfahren zur Herstellung von neuen Halogenallylpiperidinen - Google Patents
Verfahren zur Herstellung von neuen HalogenallylpiperidinenInfo
- Publication number
- DE1445518A1 DE1445518A1 DE19641445518 DE1445518A DE1445518A1 DE 1445518 A1 DE1445518 A1 DE 1445518A1 DE 19641445518 DE19641445518 DE 19641445518 DE 1445518 A DE1445518 A DE 1445518A DE 1445518 A1 DE1445518 A1 DE 1445518A1
- Authority
- DE
- Germany
- Prior art keywords
- hydrochloride
- piperidine
- hydroxyphenyl
- ether
- acid
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 108
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 62
- UOORRWUZONOOLO-OWOJBTEDSA-N (E)-1,3-dichloropropene Chemical compound ClC\C=C\Cl UOORRWUZONOOLO-OWOJBTEDSA-N 0.000 claims description 35
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 34
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 30
- -1 hydroxy, methoxy Chemical group 0.000 claims description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- UOORRWUZONOOLO-UHFFFAOYSA-N telone II Natural products ClCC=CCl UOORRWUZONOOLO-UHFFFAOYSA-N 0.000 claims description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 8
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 claims description 7
- 230000001476 alcoholic effect Effects 0.000 claims description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- STNLQJRBZHAGSO-UHFFFAOYSA-N 1-piperidin-4-ylethanone Chemical compound CC(=O)C1CCNCC1 STNLQJRBZHAGSO-UHFFFAOYSA-N 0.000 claims description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- NXAGXWTVITWDJE-UHFFFAOYSA-N Cl.OC=1C=C(C=CC1)C1(CCNCC1)C(=O)OC Chemical compound Cl.OC=1C=C(C=CC1)C1(CCNCC1)C(=O)OC NXAGXWTVITWDJE-UHFFFAOYSA-N 0.000 claims description 3
- 239000013078 crystal Substances 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- ROFVJSWBDQUQGW-UHFFFAOYSA-N piperidin-1-ium;bromide Chemical compound Br.C1CCNCC1 ROFVJSWBDQUQGW-UHFFFAOYSA-N 0.000 claims description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 10
- 229910052801 chlorine Inorganic materials 0.000 claims 10
- 239000000460 chlorine Substances 0.000 claims 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 8
- 229910052794 bromium Inorganic materials 0.000 claims 8
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 239000007795 chemical reaction product Substances 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 230000007062 hydrolysis Effects 0.000 claims 4
- 238000006460 hydrolysis reaction Methods 0.000 claims 4
- 239000003960 organic solvent Substances 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 230000029936 alkylation Effects 0.000 claims 3
- 238000005804 alkylation reaction Methods 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 125000002560 nitrile group Chemical group 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 230000010933 acylation Effects 0.000 claims 2
- 238000005917 acylation reaction Methods 0.000 claims 2
- 239000002168 alkylating agent Substances 0.000 claims 2
- 229940100198 alkylating agent Drugs 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 2
- 125000000468 ketone group Chemical group 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
- 150000003053 piperidines Chemical class 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 238000007127 saponification reaction Methods 0.000 claims 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims 1
- 241000252067 Megalops atlanticus Species 0.000 claims 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 claims 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 229960005070 ascorbic acid Drugs 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000008298 dragée Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000000839 emulsion Substances 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 230000007717 exclusion Effects 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- DJWXXFICMKSNSI-UHFFFAOYSA-N fluoro 2-hydroxy-2-methoxyacetate Chemical compound OC(C(=O)OF)OC DJWXXFICMKSNSI-UHFFFAOYSA-N 0.000 claims 1
- QWLICVXJMVMDDQ-UHFFFAOYSA-N fluoro acetate Chemical compound CC(=O)OF QWLICVXJMVMDDQ-UHFFFAOYSA-N 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 125000004969 haloethyl group Chemical group 0.000 claims 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
- 229940071870 hydroiodic acid Drugs 0.000 claims 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 230000010354 integration Effects 0.000 claims 1
- 150000002576 ketones Chemical class 0.000 claims 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 235000010755 mineral Nutrition 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 229960005181 morphine Drugs 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 239000003760 tallow Substances 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 13
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- JVNZUEVMRPWHLF-NSCUHMNNSA-N (e)-1,2-dibromoprop-1-ene Chemical compound C\C(Br)=C/Br JVNZUEVMRPWHLF-NSCUHMNNSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
- BJTDPLRIKDSWIS-UHFFFAOYSA-N 1-[4-(3-hydroxyphenyl)piperidin-4-yl]propan-1-one Chemical compound C=1C=CC(O)=CC=1C1(C(=O)CC)CCNCC1 BJTDPLRIKDSWIS-UHFFFAOYSA-N 0.000 description 2
- MLOPJPKEWAYLTG-UHFFFAOYSA-N 1-piperidin-1-ium-1-ylethanone;chloride Chemical compound Cl.CC(=O)N1CCCCC1 MLOPJPKEWAYLTG-UHFFFAOYSA-N 0.000 description 2
- DXBARFJIQSCEJG-UHFFFAOYSA-N 1-piperidin-4-ylpropan-1-one;hydrochloride Chemical compound Cl.CCC(=O)C1CCNCC1 DXBARFJIQSCEJG-UHFFFAOYSA-N 0.000 description 2
- FALCMQXTWHPRIH-UHFFFAOYSA-N 2,3-dichloroprop-1-ene Chemical compound ClCC(Cl)=C FALCMQXTWHPRIH-UHFFFAOYSA-N 0.000 description 2
- LXKNAUOWEJWGTE-UHFFFAOYSA-N 2-(3-methoxyphenyl)acetonitrile Chemical compound COC1=CC=CC(CC#N)=C1 LXKNAUOWEJWGTE-UHFFFAOYSA-N 0.000 description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- KDISMIMTGUMORD-UHFFFAOYSA-N N-acetylpiperidine Natural products CC(=O)N1CCCCC1 KDISMIMTGUMORD-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- UEALHCIWELNDMN-UHFFFAOYSA-N ethyl piperidin-1-ium-1-carboxylate;chloride Chemical compound Cl.CCOC(=O)N1CCCCC1 UEALHCIWELNDMN-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- HIILBTHBHCLUER-IWQZZHSRSA-N (z)-1,2,3-trichloroprop-1-ene Chemical compound ClC\C(Cl)=C\Cl HIILBTHBHCLUER-IWQZZHSRSA-N 0.000 description 1
- KOOLZYMTAJTCEP-UHFFFAOYSA-N 1-[4-(3-chlorophenyl)piperidin-4-yl]ethanone;hydrochloride Chemical compound [Cl-].C=1C=CC(Cl)=CC=1C1(C(=O)C)CC[NH2+]CC1 KOOLZYMTAJTCEP-UHFFFAOYSA-N 0.000 description 1
- QFGOTQUZCZHWRM-UHFFFAOYSA-N 1-[4-(3-chlorophenyl)piperidin-4-yl]propan-1-one;hydrochloride Chemical compound Cl.C=1C=CC(Cl)=CC=1C1(C(=O)CC)CCNCC1 QFGOTQUZCZHWRM-UHFFFAOYSA-N 0.000 description 1
- ZPTZXZUTZGIAHZ-UHFFFAOYSA-N 1-[4-(3-hydroxyphenyl)piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=CC=CC(O)=C1 ZPTZXZUTZGIAHZ-UHFFFAOYSA-N 0.000 description 1
- SGRBANGQRRLXOU-UHFFFAOYSA-N 1-[4-(3-methoxyphenyl)piperidin-4-yl]propan-1-one Chemical compound C=1C=CC(OC)=CC=1C1(C(=O)CC)CCNCC1 SGRBANGQRRLXOU-UHFFFAOYSA-N 0.000 description 1
- UKISZVOZHQJVLR-UHFFFAOYSA-N 1-[4-(4-methylphenyl)piperidin-4-yl]ethanone hydrochloride Chemical compound Cl.CC1=CC=C(C=C1)C1(CCNCC1)C(C)=O UKISZVOZHQJVLR-UHFFFAOYSA-N 0.000 description 1
- NNQDMQVWOWCVEM-UHFFFAOYSA-N 1-bromoprop-1-ene Chemical compound CC=CBr NNQDMQVWOWCVEM-UHFFFAOYSA-N 0.000 description 1
- FMFKNGWZEQOWNK-UHFFFAOYSA-N 1-butoxypropan-2-yl 2-(2,4,5-trichlorophenoxy)propanoate Chemical compound CCCCOCC(C)OC(=O)C(C)OC1=CC(Cl)=C(Cl)C=C1Cl FMFKNGWZEQOWNK-UHFFFAOYSA-N 0.000 description 1
- MTJVUMGKHCIMJL-UHFFFAOYSA-N 1-piperidin-1-ylpropan-1-one Chemical compound CCC(=O)N1CCCCC1 MTJVUMGKHCIMJL-UHFFFAOYSA-N 0.000 description 1
- JUCQWIKMCPCEQM-UHFFFAOYSA-N 1-piperidin-1-ylpropan-1-one;hydrochloride Chemical compound Cl.CCC(=O)N1CCCCC1 JUCQWIKMCPCEQM-UHFFFAOYSA-N 0.000 description 1
- IKRIFOGVLOSHNH-UHFFFAOYSA-N 1-piperidin-4-ylpropan-1-one Chemical compound CCC(=O)C1CCNCC1 IKRIFOGVLOSHNH-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- YMDZDFSUDFLGMX-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)ethanamine;hydron;chloride Chemical compound [Cl-].ClCC[NH2+]CCCl YMDZDFSUDFLGMX-UHFFFAOYSA-N 0.000 description 1
- VRTNIWBNFSHDEB-UHFFFAOYSA-N 3,3-dichloroprop-1-ene Chemical compound ClC(Cl)C=C VRTNIWBNFSHDEB-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- GSESKTXFZUCTQK-UHFFFAOYSA-N Cl.CC1=C(C=CC=C1)C1(CCNCC1)C(CC)=O Chemical compound Cl.CC1=C(C=CC=C1)C1(CCNCC1)C(CC)=O GSESKTXFZUCTQK-UHFFFAOYSA-N 0.000 description 1
- PMNVTKCVUHJHLO-UHFFFAOYSA-N Cl.CC1=CC=C(C=C1)C1(CCNCC1)C(CC)=O Chemical compound Cl.CC1=CC=C(C=C1)C1(CCNCC1)C(CC)=O PMNVTKCVUHJHLO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- SNZAKTXWTXRXNI-UHFFFAOYSA-N ethyl piperidine-4-carboxylate;hydrochloride Chemical compound Cl.CCOC(=O)C1CCNCC1 SNZAKTXWTXRXNI-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 150000004658 ketimines Chemical class 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- XAVNWNCTXQDFLF-UHFFFAOYSA-N methyl piperidin-1-ium-4-carboxylate;chloride Chemical compound Cl.COC(=O)C1CCNCC1 XAVNWNCTXQDFLF-UHFFFAOYSA-N 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- QRQVEZMBJQOBSI-UHFFFAOYSA-N piperidin-2-ylidenemethanone;hydrochloride Chemical compound Cl.O=C=C1CCCCN1 QRQVEZMBJQOBSI-UHFFFAOYSA-N 0.000 description 1
- PEJQONSEOMNSCK-UHFFFAOYSA-N piperidine-1-carbonitrile hydrochloride Chemical compound [Cl-].C(#N)[NH+]1CCCCC1 PEJQONSEOMNSCK-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- UJPYORPWLHQACF-UHFFFAOYSA-N propyl piperidine-1-carboxylate hydrochloride Chemical compound Cl.CCCOC(=O)N1CCCCC1 UJPYORPWLHQACF-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/64—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having an aryl radical as the second substituent in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0075148 | 1964-01-24 | ||
| DEB0075540 | 1964-02-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1445518A1 true DE1445518A1 (de) | 1968-12-05 |
Family
ID=25966942
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641445518 Pending DE1445518A1 (de) | 1964-01-24 | 1964-01-24 | Verfahren zur Herstellung von neuen Halogenallylpiperidinen |
| DE19641445520 Pending DE1445520A1 (de) | 1964-01-24 | 1964-02-21 | Verfahren zur Herstellung von substituierten 1-Alkenylpiperidinen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19641445520 Pending DE1445520A1 (de) | 1964-01-24 | 1964-02-21 | Verfahren zur Herstellung von substituierten 1-Alkenylpiperidinen |
Country Status (8)
| Country | Link |
|---|---|
| BE (1) | BE658583A (enrdf_load_stackoverflow) |
| CH (3) | CH512469A (enrdf_load_stackoverflow) |
| DE (2) | DE1445518A1 (enrdf_load_stackoverflow) |
| DK (3) | DK118283B (enrdf_load_stackoverflow) |
| FR (2) | FR4317M (enrdf_load_stackoverflow) |
| GB (1) | GB1076531A (enrdf_load_stackoverflow) |
| NL (1) | NL6500808A (enrdf_load_stackoverflow) |
| SE (1) | SE323370B (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH492710A (de) * | 1968-01-11 | 1970-06-30 | Geigy Ag J R | Verfahren zur Herstellung von neuen Piperidinderivaten |
| CH491918A (de) * | 1968-01-11 | 1970-06-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen Piperidinderivaten |
| GB9924797D0 (en) * | 1999-10-20 | 1999-12-22 | West Pharm Serv Drug Res Ltd | Compound |
-
1964
- 1964-01-24 DE DE19641445518 patent/DE1445518A1/de active Pending
- 1964-02-21 DE DE19641445520 patent/DE1445520A1/de active Pending
-
1965
- 1965-01-15 GB GB195965A patent/GB1076531A/en not_active Expired
- 1965-01-20 BE BE658583D patent/BE658583A/xx unknown
- 1965-01-20 FR FR2645A patent/FR4317M/fr not_active Expired
- 1965-01-20 FR FR2646A patent/FR1455818A/fr not_active Expired
- 1965-01-21 CH CH1748267A patent/CH512469A/de not_active IP Right Cessation
- 1965-01-21 CH CH1147671A patent/CH512470A/de not_active IP Right Cessation
- 1965-01-21 CH CH86565A patent/CH453358A/de unknown
- 1965-01-22 NL NL6500808A patent/NL6500808A/xx unknown
- 1965-01-22 SE SE85665A patent/SE323370B/xx unknown
- 1965-01-23 DK DK38565A patent/DK118283B/da unknown
- 1965-12-30 DK DK670065A patent/DK121373B/da unknown
-
1966
- 1966-11-04 DK DK575566A patent/DK115392B/da unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH512470A (de) | 1971-09-15 |
| FR1455818A (fr) | 1966-10-21 |
| DK118283B (da) | 1970-08-03 |
| DK121373B (da) | 1971-10-11 |
| SE323370B (enrdf_load_stackoverflow) | 1970-05-04 |
| NL6500808A (enrdf_load_stackoverflow) | 1965-07-26 |
| DE1445520A1 (de) | 1968-12-12 |
| FR4317M (enrdf_load_stackoverflow) | 1966-09-05 |
| GB1076531A (en) | 1967-07-19 |
| BE658583A (enrdf_load_stackoverflow) | 1965-07-20 |
| DK115392B (da) | 1969-10-06 |
| CH512469A (de) | 1971-09-15 |
| CH453358A (de) | 1968-06-14 |
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