Acrylonitrile → 3-[(1-benzyl-4-piperidyl)oxy]propanenitrile

HRID 397661Notes

Reaction equation

HRID 397661 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15](#[N:18])[CH:16]=[CH2:17]>ClCCl.[H-].[Na+]>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:17][CH2:16][C:15]#[N:18])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 7855Acrylonitrile2×HCID 784611-Benzylpiperidin-4-ol

Product 1

HCID 27945993-[(1-benzyl-4-piperidyl)oxy]propanenitrileYield 60.3%

Reagents, catalysts & solvents 2

HCID 24758Sodium hydrideCatalystHCID 6344DichloromethaneSolvent

Procedure

Sodium hydride [50% w/w in mineral oil] (2.0 g) was added to a slurry of 1-benzyl-4-piperidinol (400 g) and acrylonitrile (530 g) at 0° C. over 1 hour. The reaction mixture was warmed slowly to room temperature and stirred for 18 hours after which time the acrylonitrile was removed under reduced pressure and the residue taken up in isopropanol (1 L). The resulting yellow precipitate was filtered off. The filtrate was evaporated under reduced pressure to afford an orange oil which was dissolved in dichloromethane and washed with water. The organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by distillation to afford 2-[(1-benzyl-4-piperidyl)oxy]ethyl cyanide (308 g), b.p. 150-160° C. @ 0.2 mmHg.

Workup

  1. customwas removed under reduced pressure
  2. filtrationThe resulting yellow precipitate was filtered off
  3. customThe filtrate was evaporated under reduced pressure
  4. customto afford an orange oil which
  5. washwashed with water
  6. customThe organic layer was separated
  7. dry with materialdried over magnesium sulphate
  8. customthe solvent removed under reduced pressure
  9. distillationThe crude product was purified by distillation

Sources & evidence

ORD record
ord-5e4dc21940fe47e89aec2a98da74bdc9
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

Loading…