JPS59110656A - 光学活性な１―フェニル―２―（パラ―トリル）エチルアミンの製造方法 - Google Patents
光学活性な１―フェニル―２―（パラ―トリル）エチルアミンの製造方法Info
- Publication number
- JPS59110656A JPS59110656A JP21987682A JP21987682A JPS59110656A JP S59110656 A JPS59110656 A JP S59110656A JP 21987682 A JP21987682 A JP 21987682A JP 21987682 A JP21987682 A JP 21987682A JP S59110656 A JPS59110656 A JP S59110656A
- Authority
- JP
- Japan
- Prior art keywords
- pte
- salt
- ethylamine
- tolyl
- phenyl
- 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 16
- ZICDZTXDTPZBKH-UHFFFAOYSA-N 2-(4-methylphenyl)-1-phenylethanamine Chemical compound C1=CC(C)=CC=C1CC(N)C1=CC=CC=C1 ZICDZTXDTPZBKH-UHFFFAOYSA-N 0.000 title claims 2
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 claims abstract description 7
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 claims abstract description 6
- 229960002510 mandelic acid Drugs 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 8
- WISBVPAFDHAZAM-UHFFFAOYSA-N n-[2-(4-methylphenyl)ethyl]aniline Chemical compound C1=CC(C)=CC=C1CCNC1=CC=CC=C1 WISBVPAFDHAZAM-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 9
- 239000002253 acid Substances 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 2
- 150000007513 acids Chemical class 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 239000002917 insecticide Substances 0.000 abstract description 2
- 150000002576 ketones Chemical class 0.000 abstract description 2
- IWYDHOAUDWTVEP-SSDOTTSWSA-N (R)-mandelic acid Chemical compound OC(=O)[C@H](O)C1=CC=CC=C1 IWYDHOAUDWTVEP-SSDOTTSWSA-N 0.000 abstract 1
- XLOPRKKSAJMMEW-UHFFFAOYSA-N chrysanthemic acid Chemical compound CC(C)=CC1C(C(O)=O)C1(C)C XLOPRKKSAJMMEW-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 9
- 239000012046 mixed solvent Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000012452 mother liquor Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-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
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- 235000007516 Chrysanthemum Nutrition 0.000 description 1
- 244000189548 Chrysanthemum x morifolium Species 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 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
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21987682A JPS59110656A (ja) | 1982-12-15 | 1982-12-15 | 光学活性な１―フェニル―２―（パラ―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 |
|---|---|---|---|
| JP21987682A JPS59110656A (ja) | 1982-12-15 | 1982-12-15 | 光学活性な１―フェニル―２―（パラ―トリル）エチルアミンの製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59110656A true JPS59110656A (ja) | 1984-06-26 |
| JPH0350742B2 JPH0350742B2 (enrdf_load_stackoverflow) | 1991-08-02 |
Family
ID=16742440
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21987682A Granted JPS59110656A (ja) | 1982-12-15 | 1982-12-15 | 光学活性な１―フェニル―２―（パラ―トリル）エチルアミンの製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59110656A (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07316154A (ja) * | 1991-01-03 | 1995-12-05 | Pfizer Inc | ２−ジフェニルメチル−ｎ−［（２−メトキシフェニル）メチル−１−アザビシクロ［２，２，２オクタン−３−アミンのシス化合物のラセミ混合物の分割方法 |
| WO2005030730A1 (ja) * | 2003-09-29 | 2005-04-07 | Yamakawa Chemical Industry Co., Ltd. | 光学活性なα−アミノ−ε−カプロラクタムまたはその塩の製造方法および製造の中間体 |
| WO2008111631A1 (ja) * | 2007-03-14 | 2008-09-18 | Nippon Shinyaku Co., Ltd. | α－メチルベンジルアミン塩の製法 |
| CN104151171A (zh) * | 2014-08-14 | 2014-11-19 | 陈永军 | 一种拆分制备光学纯r-1-萘乙胺的方法 |
-
1982
- 1982-12-15 JP JP21987682A patent/JPS59110656A/ja active Granted
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07316154A (ja) * | 1991-01-03 | 1995-12-05 | Pfizer Inc | ２−ジフェニルメチル−ｎ−［（２−メトキシフェニル）メチル−１−アザビシクロ［２，２，２オクタン−３−アミンのシス化合物のラセミ混合物の分割方法 |
| WO2005030730A1 (ja) * | 2003-09-29 | 2005-04-07 | Yamakawa Chemical Industry Co., Ltd. | 光学活性なα−アミノ−ε−カプロラクタムまたはその塩の製造方法および製造の中間体 |
| JP2005104874A (ja) * | 2003-09-29 | 2005-04-21 | Yamakawa Yakuhin Kogyo Kk | 光学活性なα−アミノ−ε−カプロラクタムまたはその塩の製造方法および製造の中間体 |
| WO2008111631A1 (ja) * | 2007-03-14 | 2008-09-18 | Nippon Shinyaku Co., Ltd. | α－メチルベンジルアミン塩の製法 |
| CN104151171A (zh) * | 2014-08-14 | 2014-11-19 | 陈永军 | 一种拆分制备光学纯r-1-萘乙胺的方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0350742B2 (enrdf_load_stackoverflow) | 1991-08-02 |
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