JPH0226624B2 - - Google Patents
Info
- Publication number
- JPH0226624B2 JPH0226624B2 JP4165781A JP4165781A JPH0226624B2 JP H0226624 B2 JPH0226624 B2 JP H0226624B2 JP 4165781 A JP4165781 A JP 4165781A JP 4165781 A JP4165781 A JP 4165781A JP H0226624 B2 JPH0226624 B2 JP H0226624B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- diphenylmethylene
- formula
- purified
- above formula
- 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
- LXOFBDVFIUUFNZ-UHFFFAOYSA-N 4,4-diphenylbut-3-en-1-amine Chemical class C=1C=CC=CC=1C(=CCCN)C1=CC=CC=C1 LXOFBDVFIUUFNZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 12
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 7
- -1 vinyl compound Chemical class 0.000 description 7
- 239000002262 Schiff base Substances 0.000 description 6
- 150000004753 Schiff bases Chemical class 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 229920002554 vinyl polymer Polymers 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- VRLJFRODHVSTIK-UHFFFAOYSA-N 2-(benzhydrylideneamino)acetonitrile Chemical compound C=1C=CC=CC=1C(=NCC#N)C1=CC=CC=C1 VRLJFRODHVSTIK-UHFFFAOYSA-N 0.000 description 4
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 150000001413 amino acids Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- QUGJYNGNUBHTNS-UHFFFAOYSA-N ethyl 2-(benzhydrylideneamino)acetate Chemical compound C=1C=CC=CC=1C(=NCC(=O)OCC)C1=CC=CC=C1 QUGJYNGNUBHTNS-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000009435 amidation Effects 0.000 description 2
- 238000007112 amidation reaction Methods 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- GXLWIGXVDAJHKX-UHFFFAOYSA-N diethyl 2-(benzhydrylideneamino)pentanedioate Chemical compound C=1C=CC=CC=1C(=NC(CCC(=O)OCC)C(=O)OCC)C1=CC=CC=C1 GXLWIGXVDAJHKX-UHFFFAOYSA-N 0.000 description 2
- 235000013922 glutamic acid Nutrition 0.000 description 2
- 239000004220 glutamic acid Substances 0.000 description 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- BLOBPFFXHQZDGL-UHFFFAOYSA-N 2-(benzhydrylideneamino)acetic acid Chemical class C=1C=CC=CC=1C(=NCC(=O)O)C1=CC=CC=C1 BLOBPFFXHQZDGL-UHFFFAOYSA-N 0.000 description 1
- LUECHVCIYWADPL-UHFFFAOYSA-N 2-(benzhydrylideneamino)pentanedinitrile Chemical compound C=1C=CC=CC=1C(=NC(CCC#N)C#N)C1=CC=CC=C1 LUECHVCIYWADPL-UHFFFAOYSA-N 0.000 description 1
- LCGISIDBXHGCDW-UHFFFAOYSA-N 2-aminopentanediamide Chemical compound NC(=O)C(N)CCC(N)=O LCGISIDBXHGCDW-UHFFFAOYSA-N 0.000 description 1
- URFFPMVEWYZUQJ-UHFFFAOYSA-N 4-(benzhydrylideneamino)-4-cyanobutanamide Chemical compound C=1C=CC=CC=1C(=NC(CCC(=O)N)C#N)C1=CC=CC=C1 URFFPMVEWYZUQJ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Natural products NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- DFNYGALUNNFWKJ-UHFFFAOYSA-N aminoacetonitrile Chemical compound NCC#N DFNYGALUNNFWKJ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- ONDMKQWGMAVUNZ-UHFFFAOYSA-N butyl 2-aminoacetate Chemical compound CCCCOC(=O)CN ONDMKQWGMAVUNZ-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- SKMPRICWLXUMRY-UHFFFAOYSA-N ethyl 2-(benzhydrylideneamino)-4-cyanobutanoate Chemical compound C=1C=CC=CC=1C(=NC(CCC#N)C(=O)OCC)C1=CC=CC=C1 SKMPRICWLXUMRY-UHFFFAOYSA-N 0.000 description 1
- ASILPPKRZQUBAH-UHFFFAOYSA-N ethyl 2-amino-4-cyanobutanoate Chemical compound CCOC(=O)C(N)CCC#N ASILPPKRZQUBAH-UHFFFAOYSA-N 0.000 description 1
- WNMGEOGJKAIARK-UHFFFAOYSA-N ethyl 4-(benzhydrylideneamino)-4-cyanobutanoate Chemical compound C=1C=CC=CC=1C(=NC(CCC(=O)OCC)C#N)C1=CC=CC=C1 WNMGEOGJKAIARK-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- PQTOLHHWLUCKSB-UHFFFAOYSA-N methyl 2-(benzhydrylideneamino)acetate Chemical compound C=1C=CC=CC=1C(=NCC(=O)OC)C1=CC=CC=C1 PQTOLHHWLUCKSB-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- JJZVEQPPLFARFY-UHFFFAOYSA-N propyl 2-(benzhydrylideneamino)acetate Chemical compound C=1C=CC=CC=1C(=NCC(=O)OCCC)C1=CC=CC=C1 JJZVEQPPLFARFY-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical class CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4165781A JPS57156453A (en) | 1981-03-24 | 1981-03-24 | N-(diphenylmethylene)propylamine derivative |
| EP81106970A EP0047516B1 (en) | 1980-09-04 | 1981-09-04 | Propylamine derivative and process of manufacturing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4165781A JPS57156453A (en) | 1981-03-24 | 1981-03-24 | N-(diphenylmethylene)propylamine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57156453A JPS57156453A (en) | 1982-09-27 |
| JPH0226624B2 true JPH0226624B2 (hu) | 1990-06-12 |
Family
ID=12614434
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4165781A Granted JPS57156453A (en) | 1980-09-04 | 1981-03-24 | N-(diphenylmethylene)propylamine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57156453A (hu) |
-
1981
- 1981-03-24 JP JP4165781A patent/JPS57156453A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57156453A (en) | 1982-09-27 |
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