1,2,3,4-Tetrahydroquinoline → 10-methyl-7-(4-methyl-1-piperazinyl)-2,3-dihydro-1H-quino[1,8-ab][1,5]benzodiazepine

HRID 4029

Reaktionsgleichung

Reaktionsgleichung von HRID 4029
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.F[C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][C:13]=1[N+:19]([O-:21])=[O:20].[C:22](O)(=O)/C=C\C(O)=O.[N:30]1([C:39]2[CH:44]=[CH:43][C:42](F)=[CH:41][C:40]=2[NH:46][C:47]([N:49]2[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]2)=O)[C:38]2C(=CC=[CH:36][CH:37]=2)CC1>>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4][CH2:3][CH2:2]2)=[C:13]([N+:19]([O-:21])=[O:20])[CH:14]=1.[NH2:19][C:13]1[CH:14]=[C:15]([CH3:18])[CH:16]=[CH:17][C:12]=1[N:30]1[C:39]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:36][CH2:37][CH2:38]1.[CH3:22][C:42]1[CH:43]=[CH:44][C:39]2[N:1]3[CH2:2][CH2:3][CH2:4][C:5]4=[CH:6][CH:7]=[CH:8][C:9](=[C:10]34)[C:47]([N:49]3[CH2:50][CH2:51][N:52]([CH3:55])[CH2:53][CH2:54]3)=[N:46][C:40]=2[CH:41]=1

Komponenten

6

Edukt 3

HCID 694601,2,3,4-TetrahydroquinolineHCID 1362874-Fluoro-3-nitrotolueneHCID 70406853N-[2-(2,3-dihydro-1H-indol-1-yl)-5-fluorophenyl]-4-methyl-1-piperazine carboxamide maleate

Produkt 3

HCID 2012910910-methyl-7-(4-methyl-1-piperazinyl)-2,3-dihydro-1H-quino[1,8-ab][1,5]benzodiazepineHCID 212976531-(4-Methyl-2-nitrophenyl)-1,2,3,4-tetrahydroquinolineHCID 212976772-[3,4-Dihydro-1(2H)-quinolinyl]-5-methylaniline

Versuchsvorschrift

Starting with 1,2,3,4-tetrahydroquinoline and 2-fluoro-5-methylnitrobenzene and following the steps of 1a to 1f of Example 2, one may obtain, in sequence, 1-(4-methyl-2-nitrophenyl)-1,2,3,4-tetrahydroquinoline, 1-(2-amino-4-methylphenyl)-1,2,3,4-tetrahydroquinone, 1-(2-amino-4-methylphenyl)-1,2,3,4-tetrahydroquinoline, N-[2-{1-(5-methylphenyl)-1,2,3,4-tetrahydroquinolin-1-yl}]-4-methyl-1-piperazine carboxamide, and 10-methyl-7-(4-methyl-1-piperazinyl)-2,3-dihydro-1H-quino[1,8-ab][1,5]benzodiazepine.

Quellen und Nachweise

ORD-Eintrag
ord-50db5f899137486aaab10e21f98eedfe
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04723007

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