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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 230636Generated: October 26, 2026

Methyl iodide → N-[(4-bromophenyl)methyl]-N-methyl-1-pyrrolidinecarboxamide

https://huagongshe.com/reaction/230636

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantSodium hydrideHCID 24758—
ReactantN-[(4-bromophenyl)methyl]-1-pyrrolidinecarboxamideHCID 57762826—
SolventDimethylformamideHCID 6228—
ProductN-[(4-bromophenyl)methyl]-N-methyl-1-pyrrolidinecarboxamideHCID 57762825103.9%

Reaction Steps

N-[(4-bromophenyl)methyl]-1-pyrrolidinecarboxamide (230 mg, 0.81 mmol), was dissolved in dimethylformamide (2 ml) and treated at room temperature with a 60% sodium hydride suspension in mineral oil (33 mg, 0.83 mmol). This mix was stirred for 15 minutes before being treated with iodomethane (116 mg, 0.82 mmol). The resulting mix was stirred at 20° C. for a total of 16.5 hours. The reaction was quenched with water (4 ml) and extracted into ethyl acetate (4 ml). The organic layer was dried over sodium sulphate and the solvent removed under reduced pressure to give the title compound as a colourless oil (250 mg, crude). LC/Mass Spec (ES): Found 297 (ES+), retention time 2.90 mins. C13H1779BrN2O requires 296.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07566735B2
Source datasetuspto-grants-2009_07
ORD IDord-a38f9db399a94e7590119daaa674b8c7
Source noteuspto-grants-2009_07