JPH023627A - 光学活性１−メチル−３−フェニルプロピルアミンの製造法 - Google Patents
光学活性１−メチル−３−フェニルプロピルアミンの製造法Info
- Publication number
- JPH023627A JPH023627A JP14533788A JP14533788A JPH023627A JP H023627 A JPH023627 A JP H023627A JP 14533788 A JP14533788 A JP 14533788A JP 14533788 A JP14533788 A JP 14533788A JP H023627 A JPH023627 A JP H023627A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenylpropylamine
- optically active
- acylmethionine
- resolution
- 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
- WECUIGDEWBNQJJ-UHFFFAOYSA-N 4-phenylbutan-2-amine Chemical compound CC(N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 abstract description 20
- 230000003287 optical effect Effects 0.000 abstract description 12
- 239000003795 chemical substances by application Substances 0.000 abstract description 11
- 239000002904 solvent Substances 0.000 abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 9
- 150000001875 compounds Chemical class 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 3
- 239000003513 alkali Substances 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 3
- 239000002876 beta blocker Substances 0.000 abstract description 2
- 229940097320 beta blocking agent Drugs 0.000 abstract description 2
- 238000001816 cooling Methods 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- ZDAOHRKTKUNECS-LURJTMIESA-N (2s)-4-methylsulfanyl-2-(prop-2-enoylamino)butanoic acid Chemical compound CSCC[C@@H](C(O)=O)NC(=O)C=C ZDAOHRKTKUNECS-LURJTMIESA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 description 8
- WECUIGDEWBNQJJ-SECBINFHSA-N (2r)-4-phenylbutan-2-amine Chemical compound C[C@@H](N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-SECBINFHSA-N 0.000 description 7
- WECUIGDEWBNQJJ-VIFPVBQESA-N (2s)-4-phenylbutan-2-amine Chemical compound C[C@H](N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-VIFPVBQESA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- MLHBZVFOTDJTPK-UHFFFAOYSA-N n-methyl-3-phenylpropan-1-amine Chemical compound CNCCCC1=CC=CC=C1 MLHBZVFOTDJTPK-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- PPFRJEXUPZWQPI-SNVBAGLBSA-N (2r)-2-benzamido-4-methylsulfanylbutanoic acid Chemical compound CSCC[C@H](C(O)=O)NC(=O)C1=CC=CC=C1 PPFRJEXUPZWQPI-SNVBAGLBSA-N 0.000 description 1
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical compound NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- XUYPXLNMDZIRQH-LURJTMIESA-N N-acetyl-L-methionine Chemical compound CSCC[C@@H](C(O)=O)NC(C)=O XUYPXLNMDZIRQH-LURJTMIESA-N 0.000 description 1
- IDVJXKFJHUNVNB-UHFFFAOYSA-N acetonitrile;n-ethylethanamine Chemical compound CC#N.CCNCC IDVJXKFJHUNVNB-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229940099459 n-acetylmethionine Drugs 0.000 description 1
- -1 propatool Chemical compound 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14533788A JPH023627A (ja) | 1988-06-13 | 1988-06-13 | 光学活性１−メチル−３−フェニルプロピルアミンの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14533788A JPH023627A (ja) | 1988-06-13 | 1988-06-13 | 光学活性１−メチル−３−フェニルプロピルアミンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH023627A true JPH023627A (ja) | 1990-01-09 |
| JPH0470305B2 JPH0470305B2 (fr) | 1992-11-10 |
Family
ID=15382841
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14533788A Granted JPH023627A (ja) | 1988-06-13 | 1988-06-13 | 光学活性１−メチル−３−フェニルプロピルアミンの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH023627A (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011514341A (ja) * | 2008-02-27 | 2011-05-06 | クラリアント・スペシャルティ・ファイン・ケミカルズ（フランス） | 光学活性なα−アミノアセタール類の製造方法 |
-
1988
- 1988-06-13 JP JP14533788A patent/JPH023627A/ja active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011514341A (ja) * | 2008-02-27 | 2011-05-06 | クラリアント・スペシャルティ・ファイン・ケミカルズ（フランス） | 光学活性なα−アミノアセタール類の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0470305B2 (fr) | 1992-11-10 |
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