FI59988C - Foerfarande foer framstaellning av n-aminoalkyl-substituerade bensamider - Google Patents
Foerfarande foer framstaellning av n-aminoalkyl-substituerade bensamider Download PDFInfo
- Publication number
- FI59988C FI59988C FI333473A FI333473A FI59988C FI 59988 C FI59988 C FI 59988C FI 333473 A FI333473 A FI 333473A FI 333473 A FI333473 A FI 333473A FI 59988 C FI59988 C FI 59988C
- Authority
- FI
- Finland
- Prior art keywords
- group
- hexahydro
- general formula
- methoxy
- amino
- Prior art date
Links
- 238000005057 refrigeration Methods 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 9
- -1 nitro, benzylamino Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 229940054066 benzamide antipsychotics Drugs 0.000 claims description 4
- 150000003936 benzamides Chemical class 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- UIBHASVFXZQQEG-UHFFFAOYSA-N 1-amino-3-chloro-N-[2-(diethylamino)ethyl]-6-methoxycyclohexa-2,4-diene-1-carboxamide Chemical compound C(C)N(CCNC(C1(C(C=CC(=C1)Cl)OC)N)=O)CC UIBHASVFXZQQEG-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ANZFUYITCUUSSR-UHFFFAOYSA-N 1-acetamido-3-chloro-N-[2-(diethylamino)ethyl]-6-methoxycyclohexa-2,4-diene-1-carboxamide Chemical compound C(C)N(CCNC(C1(C(C=CC(=C1)Cl)OC)NC(C)=O)=O)CC ANZFUYITCUUSSR-UHFFFAOYSA-N 0.000 description 1
- BKLZIMHGYKYXFG-UHFFFAOYSA-N 1-amino-3-chloro-6-methoxycyclohexa-2,4-diene-1-carboxylic acid Chemical compound COC1C(C(=O)O)(C=C(C=C1)Cl)N BKLZIMHGYKYXFG-UHFFFAOYSA-N 0.000 description 1
- MUUMGBTWIYJVHM-UHFFFAOYSA-N 1-amino-N-(2-aminoethyl)-3-chloro-6-methoxycyclohexa-2,4-diene-1-carboxamide Chemical compound NCCNC(C1(C(C=CC(=C1)Cl)OC)N)=O MUUMGBTWIYJVHM-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- SCFPGWNMQPIFEW-UHFFFAOYSA-N 5-chloro-n-[2-(diethylamino)ethyl]-2-methoxybenzamide Chemical compound CCN(CC)CCNC(=O)C1=CC(Cl)=CC=C1OC SCFPGWNMQPIFEW-UHFFFAOYSA-N 0.000 description 1
- ZFDJBZWRYLIABZ-UHFFFAOYSA-N CCN(CC)CCNC(=O)C1(C=C(C=CC1OC)Cl)NCC2=CC=CC=C2 Chemical compound CCN(CC)CCNC(=O)C1(C=C(C=CC1OC)Cl)NCC2=CC=CC=C2 ZFDJBZWRYLIABZ-UHFFFAOYSA-N 0.000 description 1
- JWKBEUFHVGZYPX-UHFFFAOYSA-N CCN(CC)CCNC(=O)C1(C=C(C=CC1OC)Cl)[N+](=O)[O-] Chemical compound CCN(CC)CCNC(=O)C1(C=C(C=CC1OC)Cl)[N+](=O)[O-] JWKBEUFHVGZYPX-UHFFFAOYSA-N 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 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
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- AZRDSIPJJJPYHB-UHFFFAOYSA-M sodium 1-amino-3-chloro-6-methoxycyclohexa-2,4-diene-1-carboxylate Chemical compound COC1C(C(=O)[O-])(C=C(C=C1)Cl)N.[Na+] AZRDSIPJJJPYHB-UHFFFAOYSA-M 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- SDRXUONWFFNMIJ-UHFFFAOYSA-N triazatriphosphinine Chemical compound n1npppn1 SDRXUONWFFNMIJ-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10972072 | 1972-10-31 | ||
| JP10972072A JPS4969627A (enrdf_load_stackoverflow) | 1972-10-31 | 1972-10-31 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI59988B FI59988B (fi) | 1981-07-31 |
| FI59988C true FI59988C (fi) | 1981-11-10 |
Family
ID=14517500
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI333473A FI59988C (fi) | 1972-10-31 | 1973-10-26 | Foerfarande foer framstaellning av n-aminoalkyl-substituerade bensamider |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4969627A (enrdf_load_stackoverflow) |
| AR (1) | AR207632Q (enrdf_load_stackoverflow) |
| AT (1) | AT337163B (enrdf_load_stackoverflow) |
| CA (1) | CA1001168A (enrdf_load_stackoverflow) |
| DE (1) | DE2353554A1 (enrdf_load_stackoverflow) |
| FI (1) | FI59988C (enrdf_load_stackoverflow) |
| FR (1) | FR2204614B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1409686A (enrdf_load_stackoverflow) |
| IE (1) | IE38430B1 (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4808624A (en) * | 1984-06-28 | 1989-02-28 | Bristol-Myers Company | Pharmacologically active substituted benzamides |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1407055A (fr) * | 1963-03-05 | 1965-07-30 | Ile De France | Nouveau procédé de préparation de benzamides substitués |
-
1972
- 1972-10-31 JP JP10972072A patent/JPS4969627A/ja active Pending
-
1973
- 1973-01-01 AR AR25072273A patent/AR207632Q/es unknown
- 1973-10-25 DE DE19732353554 patent/DE2353554A1/de not_active Withdrawn
- 1973-10-26 FI FI333473A patent/FI59988C/fi active
- 1973-10-29 GB GB5016073A patent/GB1409686A/en not_active Expired
- 1973-10-29 IE IE193973A patent/IE38430B1/xx unknown
- 1973-10-30 AT AT914573A patent/AT337163B/de not_active IP Right Cessation
- 1973-10-30 CA CA184,632A patent/CA1001168A/en not_active Expired
- 1973-10-30 FR FR7338760A patent/FR2204614B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AR207632Q (es) | 1976-10-22 |
| AT337163B (de) | 1977-06-10 |
| ATA914573A (de) | 1976-10-15 |
| FI59988B (fi) | 1981-07-31 |
| CA1001168A (en) | 1976-12-07 |
| IE38430B1 (en) | 1978-03-15 |
| IE38430L (en) | 1974-04-30 |
| DE2353554A1 (de) | 1974-05-02 |
| FR2204614B1 (enrdf_load_stackoverflow) | 1978-06-30 |
| FR2204614A1 (enrdf_load_stackoverflow) | 1974-05-24 |
| GB1409686A (en) | 1975-10-15 |
| JPS4969627A (enrdf_load_stackoverflow) | 1974-07-05 |
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