JPS59116250A - 光学活性α―ｐ―トリルエチルアミンの製造方法 - Google Patents
光学活性α―ｐ―トリルエチルアミンの製造方法Info
- Publication number
- JPS59116250A JPS59116250A JP22640282A JP22640282A JPS59116250A JP S59116250 A JPS59116250 A JP S59116250A JP 22640282 A JP22640282 A JP 22640282A JP 22640282 A JP22640282 A JP 22640282A JP S59116250 A JPS59116250 A JP S59116250A
- Authority
- JP
- Japan
- Prior art keywords
- tolylethylamine
- optically active
- hydroxybenzoate
- alpha
- salt
- 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.)
- Granted
Links
- 230000003287 optical effect Effects 0.000 title claims abstract description 27
- UZDDXUMOXKDXNE-UHFFFAOYSA-N 1-(4-methylphenyl)ethanamine Chemical compound CC(N)C1=CC=C(C)C=C1 UZDDXUMOXKDXNE-UHFFFAOYSA-N 0.000 title abstract description 7
- FJKROLUGYXJWQN-UHFFFAOYSA-M 4-hydroxybenzoate Chemical compound OC1=CC=C(C([O-])=O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-M 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 10
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 12
- VKJXAQYPOTYDLO-UHFFFAOYSA-N 4-methylphenethylamine Chemical compound CC1=CC=C(CCN)C=C1 VKJXAQYPOTYDLO-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 abstract description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 18
- 239000013078 crystal Substances 0.000 abstract description 14
- 239000003795 chemical substances by application Substances 0.000 abstract description 8
- 239000000243 solution Substances 0.000 abstract description 8
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract description 6
- 239000013543 active substance Substances 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 238000002425 crystallisation Methods 0.000 abstract description 6
- 230000008025 crystallization Effects 0.000 abstract description 5
- 239000003085 diluting agent Substances 0.000 abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- 238000010438 heat treatment Methods 0.000 abstract description 4
- 239000007788 liquid Substances 0.000 abstract description 4
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 abstract description 3
- 239000011549 crystallization solution Substances 0.000 abstract description 2
- QEQVYIIYYNYLHC-UHFFFAOYSA-N 2-[(2,3-dihydroxybenzoyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)C1=CC=CC(O)=C1O QEQVYIIYYNYLHC-UHFFFAOYSA-N 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- -1 etc. Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- LSPHULWDVZXLIL-LDWIPMOCSA-N (?)-Camphoric acid Chemical compound CC1(C)[C@@H](C(O)=O)CC[C@@]1(C)C(O)=O LSPHULWDVZXLIL-LDWIPMOCSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- FHIATTMLFDJJKY-UHFFFAOYSA-N 2-hydroxy-1-(4-hydroxyphenyl)-2-phenylethanone Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=C(O)C=C1 FHIATTMLFDJJKY-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- OWNRRUFOJXFKCU-UHFFFAOYSA-N Bromadiolone Chemical compound C=1C=C(C=2C=CC(Br)=CC=2)C=CC=1C(O)CC(C=1C(OC2=CC=CC=C2C=1O)=O)C1=CC=CC=C1 OWNRRUFOJXFKCU-UHFFFAOYSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229960000304 folic acid Drugs 0.000 description 1
- 235000019152 folic acid Nutrition 0.000 description 1
- 239000011724 folic acid Substances 0.000 description 1
- 150000002224 folic acids Chemical class 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- RBLWMQWAHONKNC-UHFFFAOYSA-N hydroxyazanium Chemical compound O[NH3+] RBLWMQWAHONKNC-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22640282A JPS59116250A (ja) | 1982-12-24 | 1982-12-24 | 光学活性α―ｐ―トリルエチルアミンの製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22640282A JPS59116250A (ja) | 1982-12-24 | 1982-12-24 | 光学活性α―ｐ―トリルエチルアミンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59116250A true JPS59116250A (ja) | 1984-07-05 |
| JPH035382B2 JPH035382B2 (enrdf_load_stackoverflow) | 1991-01-25 |
Family
ID=16844555
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22640282A Granted JPS59116250A (ja) | 1982-12-24 | 1982-12-24 | 光学活性α―ｐ―トリルエチルアミンの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59116250A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6278554U (enrdf_load_stackoverflow) * | 1985-11-06 | 1987-05-20 | ||
| WO2007057468A1 (en) * | 2005-11-21 | 2007-05-24 | Boehringer Ingelheim International Gmbh | Method and complete system for developing formulations and the in vitro testing thereof with good predictability of the absorption in vivo, high throughput and low requirement of active substance |
| CN108658784A (zh) * | 2018-04-26 | 2018-10-16 | 联化科技股份有限公司 | (r)-1-(4-甲基苯基)乙胺的合成方法 |
-
1982
- 1982-12-24 JP JP22640282A patent/JPS59116250A/ja active Granted
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6278554U (enrdf_load_stackoverflow) * | 1985-11-06 | 1987-05-20 | ||
| WO2007057468A1 (en) * | 2005-11-21 | 2007-05-24 | Boehringer Ingelheim International Gmbh | Method and complete system for developing formulations and the in vitro testing thereof with good predictability of the absorption in vivo, high throughput and low requirement of active substance |
| CN108658784A (zh) * | 2018-04-26 | 2018-10-16 | 联化科技股份有限公司 | (r)-1-(4-甲基苯基)乙胺的合成方法 |
| CN108658784B (zh) * | 2018-04-26 | 2020-12-18 | 联化科技股份有限公司 | (r)-1-(4-甲基苯基)乙胺的合成方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH035382B2 (enrdf_load_stackoverflow) | 1991-01-25 |
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