Chloroacetonitrile → 1-Cyanomethyl-4-diphenylmethoxypiperidine

HRID 443798Notes

Reaction equation

HRID 443798 reaction equation
[C:1]1([CH:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[O:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:28][C:29]#[N:30]>CN(C)C=O>[C:29]([CH2:28][N:12]1[CH2:13][CH2:14][CH:9]([O:8][CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:10][CH2:11]1)#[N:30]

Participants

5

Reactant 3

HCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 30175844-Benzhydryloxypiperidine

Product 1

HCID 111203411-Cyanomethyl-4-diphenylmethoxypiperidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To the solution of 55.0 g of 4-diphenylmethoxy-piperidine in 250 ml of dimethylformamide, 32.0 g of anhydrous potassium carbonate are added while stirring, followed by the dropwise addition of the solution of 17.2 g of chloroacetonitrile in 25 ml of dimethylformamide and the suspension is stirred overnight at room temperature. It is concentrated, partitioned between water and diethyl ether, the organic phase washed with saturated aqueous sodium chloride, dried and evaporated. The residue is recrystallized from ethanol, to yield the 1-cyanomethyl-4-diphenylmethoxypiperidine melting at 78°-80°.

Workup

  1. stirringthe suspension is stirred overnight at room temperature
  2. concentrationIt is concentrated
  3. custompartitioned between water and diethyl ether
  4. washthe organic phase washed with saturated aqueous sodium chloride
  5. customdried
  6. customevaporated
  7. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-00937f2649e847eeac250a28461a6c71
Source dataset
uspto-grants-1981_04
Patent number
US04261990

Reaction notes

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