CH642946A5 - Process for the preparation of tryptamine compounds - Google Patents
Process for the preparation of tryptamine compounds Download PDFInfo
- Publication number
- CH642946A5 CH642946A5 CH90580A CH90580A CH642946A5 CH 642946 A5 CH642946 A5 CH 642946A5 CH 90580 A CH90580 A CH 90580A CH 90580 A CH90580 A CH 90580A CH 642946 A5 CH642946 A5 CH 642946A5
- Authority
- CH
- Switzerland
- Prior art keywords
- solution
- reaction mixture
- group
- tryptamine
- reaction
- Prior art date
Links
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical class C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 title claims description 110
- 238000000034 method Methods 0.000 title claims description 39
- -1 alkyl radicals Chemical class 0.000 claims description 78
- 229940067157 phenylhydrazine Drugs 0.000 claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 44
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 41
- DZQLQEYLEYWJIB-UHFFFAOYSA-N 4-aminobutanal Chemical compound NCCCC=O DZQLQEYLEYWJIB-UHFFFAOYSA-N 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 31
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 20
- 235000019441 ethanol Nutrition 0.000 claims description 19
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000003960 organic solvent Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 128
- 239000011541 reaction mixture Substances 0.000 description 117
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 75
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 66
- 239000013078 crystal Substances 0.000 description 39
- 238000004821 distillation Methods 0.000 description 29
- 239000000203 mixture Substances 0.000 description 27
- 239000007864 aqueous solution Substances 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- 238000002844 melting Methods 0.000 description 21
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000002253 acid Substances 0.000 description 18
- ANOPCGQVRXJHHD-UHFFFAOYSA-N 3-[3-(3-aminopropyl)-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]propan-1-amine Chemical compound C1OC(CCCN)OCC21COC(CCCN)OC2 ANOPCGQVRXJHHD-UHFFFAOYSA-N 0.000 description 16
- 238000001914 filtration Methods 0.000 description 14
- 230000008021 deposition Effects 0.000 description 12
- 150000003839 salts Chemical class 0.000 description 12
- 238000000605 extraction Methods 0.000 description 11
- 239000012429 reaction media Substances 0.000 description 11
- 238000011282 treatment Methods 0.000 description 11
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000009833 condensation Methods 0.000 description 9
- 230000005494 condensation Effects 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- DMULVCHRPCFFGV-UHFFFAOYSA-N N,N-dimethyltryptamine Chemical compound C1=CC=C2C(CCN(C)C)=CNC2=C1 DMULVCHRPCFFGV-UHFFFAOYSA-N 0.000 description 8
- NVUGEQAEQJTCIX-UHFFFAOYSA-N N-acetyltryptamine Chemical compound C1=CC=C2C(CCNC(=O)C)=CNC2=C1 NVUGEQAEQJTCIX-UHFFFAOYSA-N 0.000 description 8
- KTEDBFKQSUUOQJ-UHFFFAOYSA-N n-[2-(1h-indol-3-yl)ethyl]benzamide Chemical compound C=1NC2=CC=CC=C2C=1CCNC(=O)C1=CC=CC=C1 KTEDBFKQSUUOQJ-UHFFFAOYSA-N 0.000 description 8
- 238000007363 ring formation reaction Methods 0.000 description 8
- 150000004031 phenylhydrazines Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 5
- CAAGZPJPCKMFBD-UHFFFAOYSA-N 2-(1-methyl-3-indolyl)ethanamine Chemical compound C1=CC=C2N(C)C=C(CCN)C2=C1 CAAGZPJPCKMFBD-UHFFFAOYSA-N 0.000 description 4
- TYVAXMOICMBSMT-UHFFFAOYSA-N 4,4-dimethoxybutan-1-amine Chemical compound COC(OC)CCCN TYVAXMOICMBSMT-UHFFFAOYSA-N 0.000 description 4
- WZTCXTACYZGFJN-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-2-methylaniline Chemical compound C1(=C(C=CC=C1)NCCC1=CNC2=CC=CC=C12)C WZTCXTACYZGFJN-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000013019 agitation Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- IJHNRNKVSNWVEH-UHFFFAOYSA-N n-[2-(1h-indol-3-yl)ethyl]cyclohexanamine Chemical compound C=1NC2=CC=CC=C2C=1CCNC1CCCCC1 IJHNRNKVSNWVEH-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- MWOODERJGVWYJE-UHFFFAOYSA-N 1-methyl-1-phenylhydrazine Chemical compound CN(N)C1=CC=CC=C1 MWOODERJGVWYJE-UHFFFAOYSA-N 0.000 description 3
- LXATUVRMTAHHDX-UHFFFAOYSA-N 2-(5-chloro-1h-indol-3-yl)-n,n-dimethylethanamine Chemical compound C1=C(Cl)C=C2C(CCN(C)C)=CNC2=C1 LXATUVRMTAHHDX-UHFFFAOYSA-N 0.000 description 3
- GFLPSABXBDCMCN-UHFFFAOYSA-N 4,4-diethoxybutan-1-amine Chemical compound CCOC(OCC)CCCN GFLPSABXBDCMCN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- HANJMELOUJCIHC-UHFFFAOYSA-N N-benzyl-2-(5-methyl-1H-indol-3-yl)ethanamine Chemical compound CC1=CC=C2NC=C(CCNCC3=CC=CC=C3)C2=C1 HANJMELOUJCIHC-UHFFFAOYSA-N 0.000 description 3
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- JIKOBZRNRCOBRY-UHFFFAOYSA-N n-[2-(1h-indol-3-yl)ethyl]propanamide Chemical compound C1=CC=C2C(CCNC(=O)CC)=CNC2=C1 JIKOBZRNRCOBRY-UHFFFAOYSA-N 0.000 description 3
- WHMFFHYZTSCSFT-UHFFFAOYSA-N n-[2-(5-bromo-1h-indol-3-yl)ethyl]benzamide Chemical compound C12=CC(Br)=CC=C2NC=C1CCNC(=O)C1=CC=CC=C1 WHMFFHYZTSCSFT-UHFFFAOYSA-N 0.000 description 3
- PRRZWJAGZHENJJ-UHFFFAOYSA-N n-benzyl-2-(1h-indol-3-yl)ethanamine Chemical compound C=1NC2=CC=CC=C2C=1CCNCC1=CC=CC=C1 PRRZWJAGZHENJJ-UHFFFAOYSA-N 0.000 description 3
- RXSSCLFEUDVXKN-UHFFFAOYSA-N n-benzyl-n-[2-(1h-indol-3-yl)ethyl]acetamide Chemical compound C=1NC2=CC=CC=C2C=1CCN(C(=O)C)CC1=CC=CC=C1 RXSSCLFEUDVXKN-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- SCZGZDLUGUYLRV-UHFFFAOYSA-N (2-methylphenyl)hydrazine Chemical compound CC1=CC=CC=C1NN SCZGZDLUGUYLRV-UHFFFAOYSA-N 0.000 description 2
- NRESDXFFSNBDGP-UHFFFAOYSA-N (4-bromophenyl)hydrazine Chemical compound NNC1=CC=C(Br)C=C1 NRESDXFFSNBDGP-UHFFFAOYSA-N 0.000 description 2
- YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 2
- SQMOOVFBFVTTGF-UHFFFAOYSA-N 1-benzyl-1-phenylhydrazine Chemical compound C=1C=CC=CC=1N(N)CC1=CC=CC=C1 SQMOOVFBFVTTGF-UHFFFAOYSA-N 0.000 description 2
- XTKOGHRUORLSMB-UHFFFAOYSA-N 2-(1-benzylindol-3-yl)ethanamine Chemical compound C12=CC=CC=C2C(CCN)=CN1CC1=CC=CC=C1 XTKOGHRUORLSMB-UHFFFAOYSA-N 0.000 description 2
- CGHUQJRRADEHTQ-UHFFFAOYSA-N 2-(5-bromo-1h-indol-3-yl)ethanamine Chemical compound C1=C(Br)C=C2C(CCN)=CNC2=C1 CGHUQJRRADEHTQ-UHFFFAOYSA-N 0.000 description 2
- FVQKQPVVCKOWLM-UHFFFAOYSA-N 2-(5-chloro-1h-indol-3-yl)ethanamine Chemical compound C1=C(Cl)C=C2C(CCN)=CNC2=C1 FVQKQPVVCKOWLM-UHFFFAOYSA-N 0.000 description 2
- PYOUAIQXJALPKW-UHFFFAOYSA-N 2-(5-methyl-1H-indol-3-yl)ethanamine Chemical compound CC1=CC=C2NC=C(CCN)C2=C1 PYOUAIQXJALPKW-UHFFFAOYSA-N 0.000 description 2
- QKRNGBURTLCWBQ-UHFFFAOYSA-N 2-(7-chloro-1h-indol-3-yl)ethanamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1Cl QKRNGBURTLCWBQ-UHFFFAOYSA-N 0.000 description 2
- SGGBZKQTWMKXHD-UHFFFAOYSA-N 2-(7-methyl-1h-indol-3-yl)ethanamine Chemical compound CC1=CC=CC2=C1NC=C2CCN SGGBZKQTWMKXHD-UHFFFAOYSA-N 0.000 description 2
- DOQLCJMCQWQQHK-UHFFFAOYSA-N 4-chlorobutanal Chemical compound ClCCCC=O DOQLCJMCQWQQHK-UHFFFAOYSA-N 0.000 description 2
- XXNOGQJZAOXWAQ-UHFFFAOYSA-N 4-chlorophenylhydrazine Chemical compound NNC1=CC=C(Cl)C=C1 XXNOGQJZAOXWAQ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 241000669298 Pseudaulacaspis pentagona Species 0.000 description 2
- XDPRXKQTVXTALH-UHFFFAOYSA-N [4-(2-methylphenyl)phenyl]hydrazine Chemical compound CC1=C(C=CC=C1)C1=CC=C(NN)C=C1 XDPRXKQTVXTALH-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 2
- 239000011260 aqueous acid Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 150000002475 indoles Chemical class 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- WYFWKMQPMCPKLZ-UHFFFAOYSA-N n,n-dimethyl-2-(1-methylindol-3-yl)ethanamine Chemical compound C1=CC=C2C(CCN(C)C)=CN(C)C2=C1 WYFWKMQPMCPKLZ-UHFFFAOYSA-N 0.000 description 2
- CONGMAIJMUNLHQ-UHFFFAOYSA-N n-[2-(1h-indol-3-yl)ethyl]butanamide Chemical compound C1=CC=C2C(CCNC(=O)CCC)=CNC2=C1 CONGMAIJMUNLHQ-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000007793 ph indicator Substances 0.000 description 2
- 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 2
- 239000000843 powder Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- XAMBIJWZVIZZOG-UHFFFAOYSA-N (4-methylphenyl)hydrazine Chemical compound CC1=CC=C(NN)C=C1 XAMBIJWZVIZZOG-UHFFFAOYSA-N 0.000 description 1
- DZKUKLGGGNLHNY-UHFFFAOYSA-N 1,1-dimethoxybutane Chemical compound CCCC(OC)OC DZKUKLGGGNLHNY-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- OHLHOFXVEGZRQA-UHFFFAOYSA-N 1-(1-hydrazinylcyclohexa-2,4-dien-1-yl)ethanone Chemical compound C(C)(=O)C1(CC=CC=C1)NN OHLHOFXVEGZRQA-UHFFFAOYSA-N 0.000 description 1
- UMKLWBFJFMDZAH-UHFFFAOYSA-N 1-chloro-1-phenylhydrazine Chemical compound NN(Cl)C1=CC=CC=C1 UMKLWBFJFMDZAH-UHFFFAOYSA-N 0.000 description 1
- VTNTWBXHFCUYEF-UHFFFAOYSA-N 2-(1-phenylindol-3-yl)ethanamine Chemical compound C12=CC=CC=C2C(CCN)=CN1C1=CC=CC=C1 VTNTWBXHFCUYEF-UHFFFAOYSA-N 0.000 description 1
- JIIRFRORGHYVJG-UHFFFAOYSA-N 2-(1-phenylindol-3-yl)ethanamine;hydrochloride Chemical compound Cl.C12=CC=CC=C2C(CCN)=CN1C1=CC=CC=C1 JIIRFRORGHYVJG-UHFFFAOYSA-N 0.000 description 1
- QCUCAQZMPVIYAJ-UHFFFAOYSA-N 2-(4-methyl-1h-indol-3-yl)ethanamine Chemical compound CC1=CC=CC2=C1C(CCN)=CN2 QCUCAQZMPVIYAJ-UHFFFAOYSA-N 0.000 description 1
- RBHDFGBPJGEYCK-UHFFFAOYSA-N 2-(5-methyl-1h-indol-3-yl)ethylazanium;chloride Chemical compound Cl.CC1=CC=C2NC=C(CCN)C2=C1 RBHDFGBPJGEYCK-UHFFFAOYSA-N 0.000 description 1
- GEVXFHYJXGYXJP-UHFFFAOYSA-N 2-(6-methyl-1H-indol-3-yl)ethanamine Chemical compound CC1=CC=C2C(CCN)=CNC2=C1 GEVXFHYJXGYXJP-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- ZZGKOQRMQKGEOX-UHFFFAOYSA-N 4-morpholin-4-ylbutanal Chemical compound O=CCCCN1CCOCC1 ZZGKOQRMQKGEOX-UHFFFAOYSA-N 0.000 description 1
- GPZRBKWRRKBOAC-UHFFFAOYSA-N 55747-72-3 Chemical compound C1=C([N+]([O-])=O)C=C2C(CCN)=CNC2=C1 GPZRBKWRRKBOAC-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- KVIHHWIJHMUYBC-UHFFFAOYSA-N C(C)OC(CCCNC(CC)=O)OCC Chemical compound C(C)OC(CCCNC(CC)=O)OCC KVIHHWIJHMUYBC-UHFFFAOYSA-N 0.000 description 1
- 238000006641 Fischer synthesis reaction Methods 0.000 description 1
- 125000003047 N-acetyl group Chemical group 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005844 Thymol Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 229940124572 antihypotensive agent Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- UDSAIICHUKSCKT-UHFFFAOYSA-N bromophenol blue Chemical compound C1=C(Br)C(O)=C(Br)C=C1C1(C=2C=C(Br)C(O)=C(Br)C=2)C2=CC=CC=C2S(=O)(=O)O1 UDSAIICHUKSCKT-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- SGCKHQXLVVONCM-UHFFFAOYSA-N n-(4,4-dimethoxybutyl)acetamide Chemical compound COC(OC)CCCNC(C)=O SGCKHQXLVVONCM-UHFFFAOYSA-N 0.000 description 1
- SYJRXRVYSQCOCF-UHFFFAOYSA-N n-[2-(1h-indol-3-yl)ethyl]butan-1-amine Chemical compound C1=CC=C2C(CCNCCCC)=CNC2=C1 SYJRXRVYSQCOCF-UHFFFAOYSA-N 0.000 description 1
- LGROKZMEHJZWDU-UHFFFAOYSA-N n-amino-n-phenylnitramide Chemical compound [O-][N+](=O)N(N)C1=CC=CC=C1 LGROKZMEHJZWDU-UHFFFAOYSA-N 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- 125000000169 tricyclic heterocycle group Chemical group 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1355179A JPS55105664A (en) | 1979-02-08 | 1979-02-08 | Preparation of tryptamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH642946A5 true CH642946A5 (en) | 1984-05-15 |
Family
ID=11836294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH90580A CH642946A5 (en) | 1979-02-08 | 1980-02-05 | Process for the preparation of tryptamine compounds |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS55105664A (enrdf_load_stackoverflow) |
| BE (1) | BE881540A (enrdf_load_stackoverflow) |
| CH (1) | CH642946A5 (enrdf_load_stackoverflow) |
| DE (1) | DE3004700C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2448540A1 (enrdf_load_stackoverflow) |
| HU (1) | HU181054B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114230507A (zh) * | 2021-12-31 | 2022-03-25 | 阜阳欣奕华制药科技有限公司 | 一种5-甲氧基色胺的制备方法 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9013845D0 (en) * | 1990-06-21 | 1990-08-15 | Glaxo Group Ltd | Process |
| EP0775131A2 (de) * | 1994-08-03 | 1997-05-28 | ASTA Medica Aktiengesellschaft | Indol-, indazol-, pyridopyrrol- und pyridopyrazol-derivate mit antiasthmatischer, antiallergischer, entzündungshemmender und immunmodulierender wirkung |
| CN115667217A (zh) | 2020-05-19 | 2023-01-31 | 赛本爱尔兰有限公司 | 氘化的色胺衍生物和使用方法 |
-
1979
- 1979-02-08 JP JP1355179A patent/JPS55105664A/ja active Pending
-
1980
- 1980-02-05 BE BE0/199255A patent/BE881540A/fr not_active IP Right Cessation
- 1980-02-05 CH CH90580A patent/CH642946A5/fr not_active IP Right Cessation
- 1980-02-06 FR FR8002884A patent/FR2448540A1/fr active Granted
- 1980-02-08 DE DE19803004700 patent/DE3004700C2/de not_active Expired
- 1980-02-08 HU HU29080A patent/HU181054B/hu unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114230507A (zh) * | 2021-12-31 | 2022-03-25 | 阜阳欣奕华制药科技有限公司 | 一种5-甲氧基色胺的制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| BE881540A (fr) | 1980-05-30 |
| FR2448540A1 (fr) | 1980-09-05 |
| FR2448540B1 (enrdf_load_stackoverflow) | 1983-03-25 |
| JPS55105664A (en) | 1980-08-13 |
| DE3004700C2 (de) | 1986-01-30 |
| HU181054B (en) | 1983-05-30 |
| DE3004700A1 (de) | 1980-08-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |