JPS6353190B2 - - Google Patents
Info
- Publication number
- JPS6353190B2 JPS6353190B2 JP55034041A JP3404180A JPS6353190B2 JP S6353190 B2 JPS6353190 B2 JP S6353190B2 JP 55034041 A JP55034041 A JP 55034041A JP 3404180 A JP3404180 A JP 3404180A JP S6353190 B2 JPS6353190 B2 JP S6353190B2
- Authority
- JP
- Japan
- Prior art keywords
- represented
- ethyl
- solution
- ether
- residue
- 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
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical class NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
- 239000000243 solution Substances 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 21
- 238000001816 cooling Methods 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 15
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 13
- 239000010410 layer Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- 238000000862 absorption spectrum Methods 0.000 description 11
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- 238000000921 elemental analysis Methods 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 10
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 9
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000001035 drying Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MTEDGCWFXFZDAW-UHFFFAOYSA-N n'-methyl-n'-(oxolan-2-ylmethyl)-n-(2-phenylethyl)ethane-1,2-diamine Chemical compound C1CCOC1CN(C)CCNCCC1=CC=CC=C1 MTEDGCWFXFZDAW-UHFFFAOYSA-N 0.000 description 6
- -1 N -2-(4-propoxyphenyl)ethyl- N'-Methyl-N'-tetrahydrofurfurylethylenediamine Chemical compound 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 229960003424 phenylacetic acid Drugs 0.000 description 5
- 239000003279 phenylacetic acid Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- JPTIDUOYXJPZEM-UHFFFAOYSA-N n-[2-(4-methoxyphenyl)ethyl]-n'-methyl-n'-(oxolan-2-ylmethyl)ethane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1CCNCCN(C)CC1OCCC1 JPTIDUOYXJPZEM-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- NRPFNQUDKRYCNX-UHFFFAOYSA-N 4-methoxyphenylacetic acid Chemical compound COC1=CC=C(CC(O)=O)C=C1 NRPFNQUDKRYCNX-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- ZVVWZNFSMIFGEP-UHFFFAOYSA-N 2-(4-ethoxyphenyl)acetic acid Chemical compound CCOC1=CC=C(CC(O)=O)C=C1 ZVVWZNFSMIFGEP-UHFFFAOYSA-N 0.000 description 2
- CXJOONIFSVSFAD-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetyl chloride Chemical compound COC1=CC=C(CC(Cl)=O)C=C1 CXJOONIFSVSFAD-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 2
- LEGPZHPSIPPYIO-UHFFFAOYSA-N 3-Methoxyphenylacetic acid Chemical compound COC1=CC=CC(CC(O)=O)=C1 LEGPZHPSIPPYIO-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- WUAXWQRULBZETB-UHFFFAOYSA-N homoveratric acid Chemical compound COC1=CC=C(CC(O)=O)C=C1OC WUAXWQRULBZETB-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- BQOOXZZNPIJRAN-UHFFFAOYSA-N n'-(oxolan-2-ylmethyl)-n-(2-phenylethyl)-n'-propylethane-1,2-diamine Chemical compound C1CCOC1CN(CCC)CCNCCC1=CC=CC=C1 BQOOXZZNPIJRAN-UHFFFAOYSA-N 0.000 description 2
- ARQQAMRDNYNXMH-UHFFFAOYSA-N n'-ethyl-n'-(oxolan-2-ylmethyl)-n-(2-phenylethyl)ethane-1,2-diamine Chemical compound C1CCOC1CN(CC)CCNCCC1=CC=CC=C1 ARQQAMRDNYNXMH-UHFFFAOYSA-N 0.000 description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 2
- RLVNOVOUURWOHA-UHFFFAOYSA-N n-[2-(4-ethoxyphenyl)ethyl]-n'-ethyl-n'-(oxolan-2-ylmethyl)ethane-1,2-diamine Chemical compound C1=CC(OCC)=CC=C1CCNCCN(CC)CC1OCCC1 RLVNOVOUURWOHA-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 1
- ABROWERIMKBDEW-UHFFFAOYSA-N 2-(2-ethoxyphenyl)acetic acid Chemical compound CCOC1=CC=CC=C1CC(O)=O ABROWERIMKBDEW-UHFFFAOYSA-N 0.000 description 1
- IVEWTCACRDEAOB-UHFFFAOYSA-N 2-(2-methoxyphenyl)acetic acid Chemical compound COC1=CC=CC=C1CC(O)=O IVEWTCACRDEAOB-UHFFFAOYSA-N 0.000 description 1
- UPEWDRCXLROYOF-UHFFFAOYSA-N 2-(2-methoxyphenyl)acetyl chloride Chemical compound COC1=CC=CC=C1CC(Cl)=O UPEWDRCXLROYOF-UHFFFAOYSA-N 0.000 description 1
- JTSHPHZFTSLRTL-UHFFFAOYSA-N 2-(3,5-diethoxyphenyl)acetic acid Chemical compound CCOC1=CC(CC(O)=O)=CC(OCC)=C1 JTSHPHZFTSLRTL-UHFFFAOYSA-N 0.000 description 1
- FFPAFDDLAGTGPQ-UHFFFAOYSA-N 2-(3,5-dimethoxyphenyl)acetic acid Chemical compound COC1=CC(CC(O)=O)=CC(OC)=C1 FFPAFDDLAGTGPQ-UHFFFAOYSA-N 0.000 description 1
- HRFLULLBPLPBSW-UHFFFAOYSA-N 2-(3-ethoxyphenyl)acetic acid Chemical compound CCOC1=CC=CC(CC(O)=O)=C1 HRFLULLBPLPBSW-UHFFFAOYSA-N 0.000 description 1
- UZUYKYNVSJTWEH-UHFFFAOYSA-N 2-(3-methoxyphenyl)acetyl chloride Chemical compound COC1=CC=CC(CC(Cl)=O)=C1 UZUYKYNVSJTWEH-UHFFFAOYSA-N 0.000 description 1
- KSMJZTHNZYCQPE-UHFFFAOYSA-N 2-(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.COC1=CC=C(CCN)C=C1 KSMJZTHNZYCQPE-UHFFFAOYSA-N 0.000 description 1
- ULLCOWORODEDBK-UHFFFAOYSA-N 2-(4-propoxyphenyl)acetic acid Chemical compound CCCOC1=CC=C(CC(O)=O)C=C1 ULLCOWORODEDBK-UHFFFAOYSA-N 0.000 description 1
- YJEFUGPGWXNGTO-UHFFFAOYSA-N 2-(4-propoxyphenyl)acetyl chloride Chemical compound CCCOC1=CC=C(CC(Cl)=O)C=C1 YJEFUGPGWXNGTO-UHFFFAOYSA-N 0.000 description 1
- XKLPNZYLJDQZFY-UHFFFAOYSA-N 2-(oxolan-2-ylmethylamino)acetamide Chemical compound NC(=O)CNCC1CCCO1 XKLPNZYLJDQZFY-UHFFFAOYSA-N 0.000 description 1
- WSVXORGAOVUQRT-UHFFFAOYSA-N 2-chloro-n-[2-(4-methoxyphenyl)ethyl]acetamide Chemical compound COC1=CC=C(CCNC(=O)CCl)C=C1 WSVXORGAOVUQRT-UHFFFAOYSA-N 0.000 description 1
- KZHUULABPNPTEO-UHFFFAOYSA-N 2-methoxy-2-phenylacetamide Chemical compound COC(C(N)=O)C1=CC=CC=C1 KZHUULABPNPTEO-UHFFFAOYSA-N 0.000 description 1
- ZKQHTZSGNLANQM-UHFFFAOYSA-N 2-phenyl-2-propoxyacetamide Chemical compound CCCOC(C(N)=O)C1=CC=CC=C1 ZKQHTZSGNLANQM-UHFFFAOYSA-N 0.000 description 1
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- SYABXBWAWPQITF-UHFFFAOYSA-N 4-amino-2-phenylbutanamide Chemical compound NCCC(C(N)=O)C1=CC=CC=C1 SYABXBWAWPQITF-UHFFFAOYSA-N 0.000 description 1
- RGUKYNXWOWSRET-UHFFFAOYSA-N 4-pyrrolidin-1-ylpyridine Chemical compound C1CCCN1C1=CC=NC=C1 RGUKYNXWOWSRET-UHFFFAOYSA-N 0.000 description 1
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- URPUYLCJQOGOLM-UHFFFAOYSA-N n'-(oxolan-2-ylmethyl)-n-[2-(4-propoxyphenyl)ethyl]-n'-propylethane-1,2-diamine Chemical compound C1=CC(OCCC)=CC=C1CCNCCN(CCC)CC1OCCC1 URPUYLCJQOGOLM-UHFFFAOYSA-N 0.000 description 1
- UZXQTTITYSXQQH-UHFFFAOYSA-N n'-(oxolan-2-ylmethyl)ethane-1,2-diamine Chemical compound NCCNCC1CCCO1 UZXQTTITYSXQQH-UHFFFAOYSA-N 0.000 description 1
- UZWVDGCZTPJVIJ-UHFFFAOYSA-N n'-ethyl-n'-(oxolan-2-ylmethyl)-n-[2-(4-propoxyphenyl)ethyl]ethane-1,2-diamine Chemical compound C1=CC(OCCC)=CC=C1CCNCCN(CC)CC1OCCC1 UZWVDGCZTPJVIJ-UHFFFAOYSA-N 0.000 description 1
- CJBHBXRPFIQUTH-UHFFFAOYSA-N n'-ethyl-n-[2-(4-methoxyphenyl)ethyl]-n'-(oxolan-2-ylmethyl)ethane-1,2-diamine Chemical compound C1CCOC1CN(CC)CCNCCC1=CC=C(OC)C=C1 CJBHBXRPFIQUTH-UHFFFAOYSA-N 0.000 description 1
- JMXUJUQOHFDHMC-UHFFFAOYSA-N n-[2-(4-ethoxyphenyl)ethyl]-n'-methyl-n'-(oxolan-2-ylmethyl)ethane-1,2-diamine Chemical compound C1=CC(OCC)=CC=C1CCNCCN(C)CC1OCCC1 JMXUJUQOHFDHMC-UHFFFAOYSA-N 0.000 description 1
- WDDYPHUOAHGAKR-UHFFFAOYSA-N n-[2-(4-methoxyphenyl)ethyl]-n'-(oxolan-2-ylmethyl)-n'-propylethane-1,2-diamine Chemical compound C1CCOC1CN(CCC)CCNCCC1=CC=C(OC)C=C1 WDDYPHUOAHGAKR-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- YNOGYQAEJGADFJ-UHFFFAOYSA-N oxolan-2-ylmethanamine Chemical compound NCC1CCCO1 YNOGYQAEJGADFJ-UHFFFAOYSA-N 0.000 description 1
- IFXDDAVRUDKPBW-UHFFFAOYSA-N phenyl acetate;hydrochloride Chemical compound Cl.CC(=O)OC1=CC=CC=C1 IFXDDAVRUDKPBW-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3404180A JPS56131576A (en) | 1980-03-19 | 1980-03-19 | Novel phenylacetamide derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3404180A JPS56131576A (en) | 1980-03-19 | 1980-03-19 | Novel phenylacetamide derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56131576A JPS56131576A (en) | 1981-10-15 |
| JPS6353190B2 true JPS6353190B2 (nl) | 1988-10-21 |
Family
ID=12403228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3404180A Granted JPS56131576A (en) | 1980-03-19 | 1980-03-19 | Novel phenylacetamide derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS56131576A (nl) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3119034C1 (de) * | 1981-05-13 | 1983-03-10 | Kraftwerk Union AG, 4330 Mülheim | Elektromagnetfilter |
-
1980
- 1980-03-19 JP JP3404180A patent/JPS56131576A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS56131576A (en) | 1981-10-15 |
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