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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 556459Generated: October 25, 2026

Diisopropylethylamine → Rac-4-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-piperazine-1-carboxylic acid tert-butyl ester

https://huagongshe.com/reaction/556459

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactanttert-Butyl piperazine-1-carboxylateHCID 143452—
Reactant3-Bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-oneHCID 57507273—
SolventAcetonitrileHCID 6342—
ProductRac-4-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-yl]-piperazine-1-carboxylic acid tert-butyl esterHCID 5750730885.4%

Reaction Steps

The mixture of rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (1 g, 2.703 mmol), piperazine-1-carboxylic acid tert-butyl ester (0.604 g, 3.24 mmol) and DIPEA (0.419 g, 3.24 mmol) in acetonitrile (20 mL) was stirred at room temperature for overnight. The reaction mixture was concentrated and extracted with dichloromethane. The organic layer was dried over Na2SO4, filtered and concentrated to give 1.1 g of rac-4-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-piperazine-1-carboxylic acid tert-butyl ester. MS m/z 476 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08058269B2
Source datasetuspto-grants-2011_11
ORD IDord-2abee420dfd94137a55c2bec39004920
Source noteuspto-grants-2011_11