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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1859051Generated: November 4, 2026

Ammonium Chloride → 4-(2-Bromophenyl)-3-cyano-N-benzylpyrrolidine

https://huagongshe.com/reaction/1859051

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmonium ChlorideHCID 25517—
ReactantSodium bis(trimethylsilyl)amideHCID 2724254—
Reactant3-{Benzyl-[2-(2-bromophenyl)-2-chloroethyl]amino}propanenitrileHCID 22123208—
SolventTetrahydrofuranHCID 8028—
Product4-(2-Bromophenyl)-3-cyano-N-benzylpyrrolidineHCID 2212322296.3%

Reaction Conditions

Temperature-70 °C

Reaction Steps

The 90.2 g of product obtained in Step 3 are dissolved in tetrahydrofuran. The solution is cooled to -70° C. and 143 ml of a 2M solution of sodium hexamethyldisilazide are poured in dropwise. After 1 hour at -70° C. and then 12 hours at ambient temperature, the reaction mixture is poured into 300 ml of saturated aqueous ammonium chloride solution and then extracted with ether. The combined organic phases are washed and dried. After evaporating, 78.5 g of expected product are obtained in the form of a mixture of diastereoisomers.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06153640
Source datasetuspto-grants-2000_11
ORD IDord-325ea73bcad54a0cabe026132d93e27a
Source noteuspto-grants-2000_11