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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1406807Generated: October 31, 2026

Dichloromethane → 5-(4-Methyl-piperazin-1-ylmethyl)-1,3-dihydro-isoindole-2-carboxylic acid benzyl ester

https://huagongshe.com/reaction/1406807

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDichloromethaneHCID 6344—
Reactant1-MethylpiperazineHCID 53167—
Reactant5-Methanesulfonyloxymethyl-1,3-dihydro-isoindole-2-carboxylic acid benzyl esterHCID 57990212—
SolventWaterHCID 962—
Product5-(4-Methyl-piperazin-1-ylmethyl)-1,3-dihydro-isoindole-2-carboxylic acid benzyl esterHCID 5799020847%

Reaction Steps

DCM (33 L) and N-methylpiperazine (21.45 L, 193.4 mol) were stirred at 25° C. and the solution from step 8 added over a minimum of 30 mins such that temperature 20-30° C. After stirring the solution for a further 30 mins water (55 L) was added and the organic phase was washed with water (2×55 L). The product was extracted into 0.8M HCl (66 L) and the layers separated. The aqueous phase was washed with DCM (55 L) and then basified with 2M NaOH to pH 10-11 and the product was extracted into EtOAc (2×55 L). The combined organic phase were filtered to remove solids and the evaporated followed by azeotroping with toluene and drying to constant weight to give the title compound, 6.63 kg (47% yield, 98% pure by hplc).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08916552B2
Source datasetuspto-grants-2014_12
ORD IDord-4c6390376b86456096d76f511d586d1c
Source noteuspto-grants-2014_12