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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2202450Generated: October 26, 2026

Tert-Butylamine → 8-(2-Tert-butylamino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

https://huagongshe.com/reaction/2202450

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTert-ButylamineHCID 6385—
ReactantCesium carbonateHCID 10796—
ReactantDiethylaminoethyl chlorideHCID 13364—
Reactant8-(2-(diethylamino)ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 54580867—
Reactant8-Hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 66833861—
SolventWaterHCID 962—
SolventDimethylacetamideHCID 31374—
Product8-(2-Tert-butylamino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileHCID 49804871—

Reaction Conditions

Temperature100 °C

Reaction Steps

With the same synthesis condition as the Compound A7-17 (8-hydroxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile (Compound A6, 25 mg, 0.083 mmol) was dissolved in N,N-dimethylacetamide (1 mL), added with 2-chloroethyldiethylamine (16 mg, 1.1 eq.) and cesium carbonate (54 mg, 2 eq.) in order and stirred at 100° C. for 4 hours. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by amino silica gel column chromatography (ethyl acetate/hexane) to obtain the Compound A7-17 (8-(2-diethylamino-ethoxy)-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile) (11 mg, 32%)), the title compound was synthesized from the Compound A7-24 and tert-butyl amine.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365514B2
Source datasetuspto-grants-2016_06
ORD IDord-9438962a4ed14eb4ae69476d666df3cb
Source noteuspto-grants-2016_06