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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2230575Generated: October 29, 2026

Diisopropylethylamine → Ammonia

https://huagongshe.com/reaction/2230575

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiisopropylethylamineHCID 81531—
Reactant1-Carbobenzyloxy-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidineHCID 18465104—
Reactant4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl) [1,4]diazepane hydriodic acid saltHCID 86583887—
SolventAcetonitrileHCID 6342—
ProductAmmoniaHCID 2221%
Product1-carbobenzyloxy-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl) ethyl)-3-phenylpyrrolidineHCID 18464834—

Reaction Steps

Combine 1-carbobenzyloxy-3-phenyl-3-(2-methanesulfonyloxyethyl)pyrrolidine (10.2 g, 25.3 mmol), (1.34 g, 2.5 mmol), 4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepane hydriodic acid salt (16.5 g, 30.4 mmol), and N,N-diisopropylethylamine (18 mL, 101 mmol) in acetonitrile (300 mL). Heat to reflux. After 18 hours, evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 1/6 containing 1% concentrated aqueous ammonia to give 1-carbobenzyloxy-3-(2-(4-(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)[1,4]diazepan-1-yl) ethyl)-3-phenylpyrrolidine.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06423704B1
Source datasetuspto-grants-2002_07
ORD IDord-a13c818a818c47e69bdc5599edcbee93
Source noteuspto-grants-2002_07