HU181054B - Process for producing triptamine derivatives - Google Patents
Process for producing triptamine derivatives Download PDFInfo
- Publication number
- HU181054B HU181054B HU29080A HU29080A HU181054B HU 181054 B HU181054 B HU 181054B HU 29080 A HU29080 A HU 29080A HU 29080 A HU29080 A HU 29080A HU 181054 B HU181054 B HU 181054B
- Authority
- HU
- Hungary
- Prior art keywords
- tryptamine
- reaction mixture
- solution
- reaction
- alkyl
- Prior art date
Links
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical class C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 title claims abstract description 80
- 238000000034 method Methods 0.000 title claims abstract description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 48
- DZQLQEYLEYWJIB-UHFFFAOYSA-N 4-aminobutanal Chemical compound NCCCC=O DZQLQEYLEYWJIB-UHFFFAOYSA-N 0.000 claims abstract description 29
- -1 tryptamine compound Chemical class 0.000 claims abstract description 20
- 229940067157 phenylhydrazine Drugs 0.000 claims abstract description 18
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical group 0.000 claims abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 70
- 238000006243 chemical reaction Methods 0.000 claims description 43
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 35
- 150000004031 phenylhydrazines Chemical class 0.000 claims description 27
- 235000019441 ethanol Nutrition 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 17
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- 150000001241 acetals Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 13
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 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 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
- 239000003456 ion exchange resin Substances 0.000 claims description 2
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 23
- 230000000694 effects Effects 0.000 abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 abstract 1
- 229940124572 antihypotensive agent Drugs 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 239000005526 vasoconstrictor agent Substances 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 description 88
- 239000000243 solution Substances 0.000 description 83
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 56
- 239000013078 crystal Substances 0.000 description 26
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000004821 distillation Methods 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- KDFBGNBTTMPNIG-UHFFFAOYSA-N hydron;2-(1h-indol-3-yl)ethanamine;chloride Chemical compound Cl.C1=CC=C2C(CCN)=CNC2=C1 KDFBGNBTTMPNIG-UHFFFAOYSA-N 0.000 description 12
- 235000002639 sodium chloride Nutrition 0.000 description 12
- 238000007363 ring formation reaction Methods 0.000 description 10
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 10
- 239000002026 chloroform extract Substances 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- JOVOSQBPPZZESK-UHFFFAOYSA-N phenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1 JOVOSQBPPZZESK-UHFFFAOYSA-N 0.000 description 8
- 239000012429 reaction media Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229940038531 phenylhydrazine hydrochloride Drugs 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- GFLPSABXBDCMCN-UHFFFAOYSA-N 4,4-diethoxybutan-1-amine Chemical compound CCOC(OCC)CCCN GFLPSABXBDCMCN-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux 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
- 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 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- TYVAXMOICMBSMT-UHFFFAOYSA-N 4,4-dimethoxybutan-1-amine Chemical compound COC(OC)CCCN TYVAXMOICMBSMT-UHFFFAOYSA-N 0.000 description 3
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical class CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 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 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
- 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
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- XXNOGQJZAOXWAQ-UHFFFAOYSA-N 4-chlorophenylhydrazine Chemical compound NNC1=CC=C(Cl)C=C1 XXNOGQJZAOXWAQ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 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 2
- DACWITGQKLUJCT-UHFFFAOYSA-N n-benzyl-2-(1h-indol-3-yl)ethanamine;hydrochloride Chemical compound [Cl-].C=1NC2=CC=CC=C2C=1CC[NH2+]CC1=CC=CC=C1 DACWITGQKLUJCT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- HMHWNJGOHUYVMD-UHFFFAOYSA-N (4-methylanilino)azanium;chloride Chemical compound Cl.CC1=CC=C(NN)C=C1 HMHWNJGOHUYVMD-UHFFFAOYSA-N 0.000 description 1
- YHYKLKNNBYLTQY-UHFFFAOYSA-N 1,1-diphenylhydrazine Chemical compound C=1C=CC=CC=1N(N)C1=CC=CC=C1 YHYKLKNNBYLTQY-UHFFFAOYSA-N 0.000 description 1
- MHDIVKHYLSDJNX-UHFFFAOYSA-N 1-[2-(1h-indol-3-yl)ethyl]piperidin-2-one Chemical compound O=C1CCCCN1CCC1=CNC2=CC=CC=C12 MHDIVKHYLSDJNX-UHFFFAOYSA-N 0.000 description 1
- 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 1
- NBXGIIMMSBYDKU-UHFFFAOYSA-N 1-bromo-1-phenylhydrazine Chemical compound NN(Br)C1=CC=CC=C1 NBXGIIMMSBYDKU-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
- HXODBIRGIPGNQF-UHFFFAOYSA-N 1-oxaspiro[5.5]undecane Chemical compound C1CCCCC21OCCCC2 HXODBIRGIPGNQF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WPJRVOBVFXWOOU-UHFFFAOYSA-N 2-(1-benzylindol-3-yl)ethanamine;hydrochloride Chemical compound Cl.C12=CC=CC=C2C(CCN)=CN1CC1=CC=CC=C1 WPJRVOBVFXWOOU-UHFFFAOYSA-N 0.000 description 1
- ACQZGJPUFDESCT-UHFFFAOYSA-N 2-(1-methylindol-3-yl)ethanamine;hydrochloride Chemical compound Cl.C1=CC=C2N(C)C=C(CCN)C2=C1 ACQZGJPUFDESCT-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
- 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 1
- QUPXCOYSKSUJPX-UHFFFAOYSA-N 2-(5-bromo-1h-indol-3-yl)ethanamine;hydrochloride Chemical compound Cl.C1=C(Br)C=C2C(CCN)=CNC2=C1 QUPXCOYSKSUJPX-UHFFFAOYSA-N 0.000 description 1
- PBANXRNIXGEHPZ-UHFFFAOYSA-N 2-(5-chloro-1h-indol-3-yl)ethanamine;hydron;chloride Chemical compound Cl.C1=C(Cl)C=C2C(CCN)=CNC2=C1 PBANXRNIXGEHPZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- TXIDBOZNQRWNOE-UHFFFAOYSA-N 2-(7-chloro-1h-indol-3-yl)ethanamine;hydrochloride Chemical compound Cl.C1=CC=C2C(CCN)=CNC2=C1Cl TXIDBOZNQRWNOE-UHFFFAOYSA-N 0.000 description 1
- SGGBZKQTWMKXHD-UHFFFAOYSA-N 2-(7-methyl-1h-indol-3-yl)ethanamine Chemical compound CC1=CC=CC2=C1NC=C2CCN SGGBZKQTWMKXHD-UHFFFAOYSA-N 0.000 description 1
- XXXLVXQSFKCFAL-UHFFFAOYSA-N 2-(7-methyl-1h-indol-3-yl)ethanamine;hydrochloride Chemical compound Cl.CC1=CC=CC2=C1NC=C2CCN XXXLVXQSFKCFAL-UHFFFAOYSA-N 0.000 description 1
- ADODRSVGNHNKAT-UHFFFAOYSA-N 2-Chlorophenylhydrazine hydrochloride Chemical compound Cl.NNC1=CC=CC=C1Cl ADODRSVGNHNKAT-UHFFFAOYSA-N 0.000 description 1
- FGEPRNXUNITOCW-UHFFFAOYSA-N 2-aminobutanal Chemical compound CCC(N)C=O FGEPRNXUNITOCW-UHFFFAOYSA-N 0.000 description 1
- VADKRMSMGWJZCF-UHFFFAOYSA-N 2-bromophenol Chemical compound OC1=CC=CC=C1Br VADKRMSMGWJZCF-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- GOERNKBWPMTGED-UHFFFAOYSA-N 3,9-bis(3-aminopropyl)spiro[5.5]undecane-2,4,8,10-tetrone Chemical compound C1C(=O)C(CCCN)C(=O)CC21CC(=O)C(CCCN)C(=O)C2 GOERNKBWPMTGED-UHFFFAOYSA-N 0.000 description 1
- WDEVQCOHGGWMPO-UHFFFAOYSA-N 3-[3-[3-(dimethylamino)propyl]-2,4,8,10-tetraoxaspiro[5.5]undecan-9-yl]-N,N-dimethylpropan-1-amine Chemical compound CN(CCCC1OCC2(CO1)COC(OC2)CCCN(C)C)C WDEVQCOHGGWMPO-UHFFFAOYSA-N 0.000 description 1
- KIZLFGGIXGLHSF-UHFFFAOYSA-N 4-(4,4-dimethoxybutyl)morpholine Chemical compound COC(OC)CCCN1CCOCC1 KIZLFGGIXGLHSF-UHFFFAOYSA-N 0.000 description 1
- DDSLGZOYEPKPSJ-UHFFFAOYSA-N 4-acetamidobutanal Chemical compound CC(=O)NCCCC=O DDSLGZOYEPKPSJ-UHFFFAOYSA-N 0.000 description 1
- NWRCPGDBUIUUCW-UHFFFAOYSA-N 4-amino-1-ethoxybutan-1-ol Chemical compound CCOC(O)CCCN NWRCPGDBUIUUCW-UHFFFAOYSA-N 0.000 description 1
- DOQLCJMCQWQQHK-UHFFFAOYSA-N 4-chlorobutanal Chemical compound ClCCCC=O DOQLCJMCQWQQHK-UHFFFAOYSA-N 0.000 description 1
- HXHGULXINZUGJX-UHFFFAOYSA-N 4-chlorobutanol Chemical compound OCCCCCl HXHGULXINZUGJX-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-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
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 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 1
- IKDJURJRDBCKRV-UHFFFAOYSA-N [4-(2-methylphenyl)phenyl]hydrazine hydrochloride Chemical compound CC1=CC=CC=C1C2=CC=C(C=C2)NN.Cl IKDJURJRDBCKRV-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- MIVUDWFNUOXEJM-UHFFFAOYSA-N amino(diphenyl)azanium;chloride Chemical compound Cl.C=1C=CC=CC=1N(N)C1=CC=CC=C1 MIVUDWFNUOXEJM-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000002035 hexane extract Substances 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000007522 mineralic acids Chemical class 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
- 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 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000011236 particulate material Substances 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
- 230000000704 physical effect Effects 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
- 239000012254 powdered material Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- PRZSXZWFJHEZBJ-UHFFFAOYSA-N thymol blue Chemical compound C1=C(O)C(C(C)C)=CC(C2(C3=CC=CC=C3S(=O)(=O)O2)C=2C(=CC(O)=C(C(C)C)C=2)C)=C1C PRZSXZWFJHEZBJ-UHFFFAOYSA-N 0.000 description 1
- 239000012485 toluene extract Substances 0.000 description 1
- 125000000169 tricyclic heterocycle group Chemical group 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)
- Hydrogenated Pyridines (AREA)
- Indole Compounds (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 |
|---|---|
| HU181054B true HU181054B (en) | 1983-05-30 |
Family
ID=11836294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU29080A HU181054B (en) | 1979-02-08 | 1980-02-08 | Process for producing triptamine derivatives |
Country Status (6)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9013845D0 (en) * | 1990-06-21 | 1990-08-15 | Glaxo Group Ltd | Process |
| US5965582A (en) * | 1994-08-03 | 1999-10-12 | Asta Medica Aktiengesellschaft | N-benzylindole and benzopyrazole derivatives with anti-asthmatic, anti-allergic, anti-inflammatory and immunemodulating effect |
| JP2023526856A (ja) | 2020-05-19 | 2023-06-23 | サイビン アイアールエル リミテッド | 重水素化トリプタミン誘導体および使用方法 |
| CN114230507B (zh) * | 2021-12-31 | 2024-11-12 | 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 |
-
1979
- 1979-02-08 JP JP1355179A patent/JPS55105664A/ja active Pending
-
1980
- 1980-02-05 CH CH90580A patent/CH642946A5/fr not_active IP Right Cessation
- 1980-02-05 BE BE0/199255A patent/BE881540A/fr not_active IP Right Cessation
- 1980-02-06 FR FR8002884A patent/FR2448540A1/fr active Granted
- 1980-02-08 HU HU29080A patent/HU181054B/hu unknown
- 1980-02-08 DE DE19803004700 patent/DE3004700C2/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2448540A1 (fr) | 1980-09-05 |
| BE881540A (fr) | 1980-05-30 |
| DE3004700C2 (de) | 1986-01-30 |
| FR2448540B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1983-03-25 |
| CH642946A5 (en) | 1984-05-15 |
| JPS55105664A (en) | 1980-08-13 |
| DE3004700A1 (de) | 1980-08-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |