Acrylonitrile → 3-(4-Diphenylmethylpiperidin-1-yl)propionitrile

HRID 964265Notes

Reaction equation

HRID 964265 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20](#[N:23])[CH:21]=[CH2:22]>CCO>[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]2[CH2:9][CH2:10][N:11]([CH2:22][CH2:21][C:20]#[N:23])[CH2:12][CH2:13]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 882784-Benzhydrylpiperidine

Product 1

HCID 230041313-(4-Diphenylmethylpiperidin-1-yl)propionitrileYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of diphenyl-4-piperidylmethane (810 mg, 3.22 mmol, 1.00 equiv) in EtOH (5 mL) was added acrylonitrile (0.53 mL, 8.06 mmol, 2.50 equiv) dropwise at 0° C. The mixture was stirred at room temperature for 1.5 hours and then concentrated. The residue was purified by flash chromatography (SiO2, EtOAc-hexane 9:1 to 2:1) to give 480 mg (49%) of white solid, which was characterized spectroscopically.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by flash chromatography (SiO2, EtOAc-hexane 9:1 to 2:1)

Sources & evidence

ORD record
ord-9aeac10be06440f08f8cc51c5ffe3cd3
Source dataset
uspto-grants-1998_06
Patent number
US05767131

Reaction notes

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