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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 4029Generated: October 23, 2026

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

https://huagongshe.com/en/reaction/4029

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2,3,4-TetrahydroquinolineHCID 69460—
Reactant4-Fluoro-3-nitrotolueneHCID 136287—
ReactantN-[2-(2,3-dihydro-1H-indol-1-yl)-5-fluorophenyl]-4-methyl-1-piperazine carboxamide maleateHCID 70406853—
Product10-methyl-7-(4-methyl-1-piperazinyl)-2,3-dihydro-1H-quino[1,8-ab][1,5]benzodiazepineHCID 20129109—
Product1-(4-Methyl-2-nitrophenyl)-1,2,3,4-tetrahydroquinolineHCID 21297653—
Product2-[3,4-Dihydro-1(2H)-quinolinyl]-5-methylanilineHCID 21297677—

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04723007
Source datasetuspto-grants-1988_02
ORD IDord-50db5f899137486aaab10e21f98eedfe
Source noteuspto-grants-1988_02