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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1471015Generated: October 26, 2026

Dimethylformamide → 4,4'-(1-(4-Tert-butylphenyl)pyrrolidine-2,5-diyl)dibenzonitrile

https://huagongshe.com/reaction/1471015

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantAmmonium HydroxideHCID 14923—
Reactant2,5-Bis(4-bromophenyl)-1-(4-tert-butylphenyl)pyrrolidineHCID 58226837—
ReactantHCID 178418546HCID 178418546—
SolventWaterHCID 962—
Product4,4'-(1-(4-Tert-butylphenyl)pyrrolidine-2,5-diyl)dibenzonitrileHCID 6723649478%

Reaction Steps

A solution of Example 42C (2.0 g, 3.9 mmol) and copper(I) cyanide (1.047 g, 11.69 mmol) in DMF (19 mL) was heated in a microwave for 7 hours at 160° C. Afterwards the mixture was poured in water (700 mL) and then concentrated ammonium hydroxide (40 mL) was added and the solution extracted with EtOAc. The organic extract was dried, filtered, concentrated and the residue purified by flash chromatography (silica gel, EtOAc/hexanes) to afford 1.23 g (78%) of the title compound. MS (ESI) m/z 406 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09006387B2
Source datasetuspto-grants-2015_04
ORD IDord-900f966cda17430b9a399a9099ce2e8c
Source noteuspto-grants-2015_04