Phosphorus oxychloride → 1-Benzylpiperidine-4-carbonitrile

HRID 2300166Notes

Reaction equation

HRID 2300166 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH2:16])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>CN(C)C=O>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]#[N:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 7831561-Benzylpiperidine-4-carboxamide

Product 1

HCID 7933831-Benzylpiperidine-4-carbonitrileYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5 ml N,N-dimethylformamide was added to a mixture of 12.7 g 1-benzyl-4-piperidine carboxamide and 60 ml phosphorus oxychloride under ice-cooling, and it was stirred at room temperature for 1.5 hr. It was evaporated, and the resulting residue was dissolved in ethyl acetate and washed with aqueous sodium hydroxide and brine. After drying over anhydrous sodium sulfate, it was evaporated, and the resulting residue was purified by silica gel column chromatography to give 11.0 g of 1-benzyl-4-piperidine carbonitrile.

Workup

  1. temperaturecooling
  2. customIt was evaporated
  3. dissolutionthe resulting residue was dissolved in ethyl acetate
  4. washwashed with aqueous sodium hydroxide and brine
  5. dry with materialAfter drying over anhydrous sodium sulfate, it
  6. customwas evaporated
  7. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b1f4c7b5410e4ddb83e77f0ff5d2f4db
Source dataset
uspto-grants-2002_12
Patent number
US06498159B1

Reaction notes

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