JPS6126982B2 - - Google Patents
Info
- Publication number
- JPS6126982B2 JPS6126982B2 JP2044781A JP2044781A JPS6126982B2 JP S6126982 B2 JPS6126982 B2 JP S6126982B2 JP 2044781 A JP2044781 A JP 2044781A JP 2044781 A JP2044781 A JP 2044781A JP S6126982 B2 JPS6126982 B2 JP S6126982B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- general formula
- represented
- integer
- group
- 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
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 6
- 150000004728 pyruvic acid derivatives Chemical class 0.000 claims description 5
- 125000005265 dialkylamine group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003495 polar organic solvent Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 229940085239 selective calcium channel blockers with direct cardiac effects phenylalkylamine derivative Drugs 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000001819 mass spectrum Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- ACSAKRLPJQIBFB-UHFFFAOYSA-N 2-phenyl-n-(2-phenylethyl)ethanamine Chemical compound C=1C=CC=CC=1CCNCCC1=CC=CC=C1 ACSAKRLPJQIBFB-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- 150000003974 aralkylamines Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- PCZDVXCOGAXAOY-UHFFFAOYSA-N 5-[2-[2-(3-hydroxy-4-methoxyphenyl)ethylamino]ethyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC=C1CCNCCC1=CC=C(OC)C(O)=C1 PCZDVXCOGAXAOY-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- BTNMPGBKDVTSJY-UHFFFAOYSA-N keto-phenylpyruvic acid Chemical compound OC(=O)C(=O)CC1=CC=CC=C1 BTNMPGBKDVTSJY-UHFFFAOYSA-N 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- RXMTUVIKZRXSSM-UHFFFAOYSA-N 2,2-diphenylethanamine Chemical class C=1C=CC=CC=1C(CN)C1=CC=CC=C1 RXMTUVIKZRXSSM-UHFFFAOYSA-N 0.000 description 1
- ZBLQKSNIFYXZTI-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)ethanamine Chemical compound CC(C)C1=CC=C(CCN)C=C1 ZBLQKSNIFYXZTI-UHFFFAOYSA-N 0.000 description 1
- MNNZINNZIQVULG-UHFFFAOYSA-N 2-chloroethylbenzene Chemical compound ClCCC1=CC=CC=C1 MNNZINNZIQVULG-UHFFFAOYSA-N 0.000 description 1
- ARBYLMGHSUQHSN-UHFFFAOYSA-N 2-oxo-3-(4-propan-2-ylphenyl)propanoic acid Chemical compound CC(C)C1=CC=C(CC(=O)C(O)=O)C=C1 ARBYLMGHSUQHSN-UHFFFAOYSA-N 0.000 description 1
- 239000001903 2-oxo-3-phenylpropanoic acid Substances 0.000 description 1
- RCMTXVVCIMZWKK-UHFFFAOYSA-N 2-phenyl-n-(2-phenylethyl)ethanimine Chemical compound C=1C=CC=CC=1CC=NCCC1=CC=CC=C1 RCMTXVVCIMZWKK-UHFFFAOYSA-N 0.000 description 1
- WGTASENVNYJZBK-UHFFFAOYSA-N 3,4,5-trimethoxyamphetamine Chemical compound COC1=CC(CC(C)N)=CC(OC)=C1OC WGTASENVNYJZBK-UHFFFAOYSA-N 0.000 description 1
- RRKRGSNBJQKLOR-UHFFFAOYSA-N 3-(3-hydroxy-4-methoxyphenyl)-2-oxopropanoic acid Chemical compound COC1=CC=C(CC(=O)C(O)=O)C=C1O RRKRGSNBJQKLOR-UHFFFAOYSA-N 0.000 description 1
- VRYUGTMBOLOQTA-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-oxopropanoic acid Chemical compound OC(=O)C(=O)CC1=CC=C(Cl)C=C1 VRYUGTMBOLOQTA-UHFFFAOYSA-N 0.000 description 1
- QRXPIKKZQGWJMW-ZETCQYMHSA-N 4-O-methyl-L-dopa zwitterion Chemical compound COC1=CC=C(C[C@H](N)C(O)=O)C=C1O QRXPIKKZQGWJMW-ZETCQYMHSA-N 0.000 description 1
- WJXQFVMTIGJBFX-UHFFFAOYSA-N 4-methoxytyramine Chemical compound COC1=CC=C(CCN)C=C1O WJXQFVMTIGJBFX-UHFFFAOYSA-N 0.000 description 1
- KAAFITWSSODFMA-UHFFFAOYSA-N 5-(2-aminoethyl)-2-methoxyphenol;hydron;chloride Chemical compound [Cl-].COC1=CC=C(CC[NH3+])C=C1O KAAFITWSSODFMA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- DEDGUGJNLNLJSR-UHFFFAOYSA-N alpha-hydroxycinnamic acid Natural products OC(=O)C(O)=CC1=CC=CC=C1 DEDGUGJNLNLJSR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- -1 hydroxy-4-methoxyphenyl Chemical group 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229940117803 phenethylamine Drugs 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing 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 |
|---|---|---|---|
| JP2044781A JPS57134448A (en) | 1981-02-14 | 1981-02-14 | Production of diaralkylamine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2044781A JPS57134448A (en) | 1981-02-14 | 1981-02-14 | Production of diaralkylamine |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57134448A JPS57134448A (en) | 1982-08-19 |
| JPS6126982B2 true JPS6126982B2 (enrdf_load_stackoverflow) | 1986-06-23 |
Family
ID=12027305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2044781A Granted JPS57134448A (en) | 1981-02-14 | 1981-02-14 | Production of diaralkylamine |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57134448A (enrdf_load_stackoverflow) |
-
1981
- 1981-02-14 JP JP2044781A patent/JPS57134448A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57134448A (en) | 1982-08-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU1005655A3 (ru) | Способ получени 3-арилокси-3-фенилпропиламинов или их солей | |
| SU1333234A3 (ru) | Способ получени производных N-фенилбензамида или их солей | |
| US4963679A (en) | Process for preparing bis (3,5-dioxopiperazinyl) alkanes or alkenes | |
| JPS6126982B2 (enrdf_load_stackoverflow) | ||
| US4247479A (en) | Process for the manufacture of aromatic amines from α, β-unsaturated cycloaliphatic ketoximes | |
| JPH10506653A (ja) | ヨウ素化造影剤の製造方法 | |
| JPS5949221B2 (ja) | ３−アシルアミノ−４−ホモイソツイスタンの製造法 | |
| WO2000064855A1 (en) | Epimerization reaction for the production of r-fluoxetine | |
| JPH11508567A (ja) | β−アミノ−α−ヒドロキシカルボン酸及びその誘導体の製造方法 | |
| US5639895A (en) | Process for producing β-nitroenamine | |
| JP2771257B2 (ja) | イミダゾール誘導体の製法 | |
| JPH0643382B2 (ja) | アミン誘導体の製法 | |
| US3124594A (en) | Cyanoalkyl | |
| RU2131872C1 (ru) | Способ получения замещенных 2-(фениламино)-2-имидазолинов | |
| NL7904774A (nl) | Werkwijze voor het bereiden van n,n'-di-gesubstiueerde 2-naftaleenethaanimidamiden. | |
| JP2767295B2 (ja) | インドール―３―カルボニトリル化合物の製造方法 | |
| JPS6210500B2 (enrdf_load_stackoverflow) | ||
| KR100441348B1 (ko) | 에피나스틴 염산염의 중간체인 6-모르판트리돈의 새로운제조방법 | |
| SU1490115A1 (ru) | Способ получени гидрохлорида N-ацетил-2-хлор-3-иминоиндолина | |
| JPS5914036B2 (ja) | リフアマイシンｓｖ誘導体の新規製造法 | |
| JPS6272680A (ja) | ラニチジン又はその酸付加塩の製造方法 | |
| HU202491B (en) | Process for producing pyrroline derivatives | |
| JPS63192747A (ja) | ホルムアミジンのギ酸塩 | |
| JPH05178834A (ja) | Ｎ−シアノアセトアミジン誘導体の製法 | |
| JPH0324045A (ja) | クロロマレエートまたはクロロフマレートまたはそれらの混合物を経るアニリノフマレートの製造方法 |