Water → (RS)-1-Benzyl-2-cyanomethylpiperidine

HRID 598554Notes

Reaction equation

HRID 598554 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-:16]#[N:17].[Na+].O>CS(C)=O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][C:16]#[N:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 231462741-Benzyl-2-(bromomethyl)piperidine

Product 1

HCID 18941050(RS)-1-Benzyl-2-cyanomethylpiperidine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
85 °C

Procedure

(RS)-1-Benzyl-2-bromomethylpiperidine, D31 (4.2 g) was dissolved in dry dimethylsulphoxide (15 ml) and treated with sodium cyanide (5.0 g). The solution was then stirred at 85° C. under argon for 18 h. The reaction solution was then poured into water (300 ml) and extracted with dichloromethane (2×200 ml). The organic solution was dried (MgSO4) and the solvent removed in vacuo. Chromatography (silica gel, diethyl ether/petroleum ether mixtures) afforded the title compound (3.3 g).

Workup

  1. extractionextracted with dichloromethane (2×200 ml)
  2. dry with materialThe organic solution was dried (MgSO4)
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-51653bc239704ea2bfe27133ab2e139e
Source dataset
uspto-grants-2011_03
Patent number
US07897618B2

Reaction notes

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