Water → 1-Benzyl-4-hydroxypiperidine-4-carbonitrile

HRID 1598995Notes

Reaction equation

HRID 1598995 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)[O-].[Na+].[C-:21]#[N:22].[K+].O>C(OCC)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([OH:14])([C:21]#[N:22])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 192201-Benzyl-4-piperidoneHCID 516919Sodium Bisulfate

Product 1

HCID 801891-Benzyl-4-hydroxypiperidine-4-carbonitrileYield 74.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A slurry of 1-benzyl-4-piperidone (53.3 g, 0.28 mol), sodium bisulfate (38.5 g, 0.32 mol), potassium cyanide (24.5 g, 0.38 mol) and water (200 mL) was stirred 1 hour and then combined with diethyl ether. The mixture was stirred 1 hour and the ether layer was separated, washed with water (2×) and brine (2×), dried (K2CO3), filtered and concentrated. The residue was crystallized from pentane/diethyl ether (3:1, approximately 400 mL) to give 1-benzyl-4-hydroxypiperidine-4-carbonitrile (45 g) as a crude material.

Workup

  1. customthe ether layer was separated
  2. washwashed with water (2×) and brine (2×)
  3. dry with materialdried (K2CO3)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was crystallized from pentane/diethyl ether (3:1, approximately 400 mL)

Sources & evidence

ORD record
ord-b9e71c18f71c4aaabb06b335656b1445
Source dataset
uspto-grants-1998_04
Patent number
US05739336

Reaction notes

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