Acrylonitrile → HCID 521362, compound

HRID 322149Notes

Reaction equation

HRID 322149 reaction equation
[OH:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:14](#[N:17])[CH:15]=[CH2:16]>CCO>[OH:1][C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][N:5]([CH2:16][CH2:15][C:14]#[N:17])[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 7855AcrylonitrileHCID 963874-Phenylpiperidin-4-ol

Product 1

HCID 521362HCID 521362, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-hydroxy-4-phenylpiperidine (3.11 g, 17.5 mmol, 1.00 equiv) in EtOH (30 mL) was added acrylonitrile (2.89 mL, 43.8 mmol, 2.50 equiv) dropwise at 0° C. The mixture was stirred at room temperature for 1.5 hours and then concentrated to afford 3.71 g (92%) of white solid, which was characterized spectroscopically.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-eed628b07df34c2db272cb9ebd920dc6
Source dataset
uspto-grants-2001_04
Patent number
US06211198B1

Reaction notes

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