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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 556464Generated: October 26, 2026

1-Methylpiperazine → Rac-6-chloro-3-(3-chloro-benzyl)-3-[3-(4-methyl-piperazine-1-carbonyl)-phenylamino]-1,3-dihydro-indol-2-one

https://huagongshe.com/reaction/556464

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-MethylpiperazineHCID 53167—
Reactant1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2723939—
ReactantRac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1h-indol-3-ylamino]-benzoic acidHCID 57507310—
ProductRac-6-chloro-3-(3-chloro-benzyl)-3-[3-(4-methyl-piperazine-1-carbonyl)-phenylamino]-1,3-dihydro-indol-2-oneHCID 24950103—

Reaction Steps

The mixture of rac-3-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-ylamino]-benzoic acid (60 mg, 0.14 mmol), 1-methyl-piperazine (56 mg, 0.56 mmol) and EDCl (54 mg, 0.28 mmol) in dichlorometahne (2 mL) was stirred at room temperature for overnight. The reaction mixture was purified by preparative HPLC to give rac-6-chloro-3-(3-chloro-benzyl)-3-[3-(4-methyl-piperazine-1-carbonyl)-phenylamino]-1,3-dihydro-indol-2-one as a powder. 1H NMR (CDCl3, 400 MHz): δ 7.21-6.74 (m, 9H), 6.49 (d, 1H), 6.17 (s, 1H), 4.70 (s, 1H), 3.80-3.45 (br, 8H), 3.28-3.15 (q, 2H), 2.66 (s, 3H). MS: [M+H]+=509

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08058269B2
Source datasetuspto-grants-2011_11
ORD IDord-593edf92791c41799641945720bc1555
Source noteuspto-grants-2011_11