Sodium Cyanide → 4-Cyanomethyl-1-diphenylmethylpiperidine

HRID 362887Notes

Reaction equation

HRID 362887 reaction equation
[C-:1]#[N:2].[Na+].[C:4]1([CH:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:11]2[CH2:16][CH2:15][CH:14]([CH2:17]Cl)[CH2:13][CH2:12]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])(O)=O.[Na+]>CS(C)=O>[C:1]([CH2:17][CH:14]1[CH2:15][CH2:16][N:11]([CH:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:12][CH2:13]1)#[N:2]

Participants

5

Reactant 3

HCID 8929Sodium CyanideHCID 516892Sodium BicarbonateHCID 538573511-Diphenylmethyl-4-chloromethylpiperidine

Product 1

HCID 184257274-Cyanomethyl-1-diphenylmethylpiperidineYield 61.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

Step 3): NaCN (2.5 g, 51 mmol) was added to a solution of 1-diphenylmethyl-4-chloromethyl-piperidine (8.9 g, 29.7 mmol) in dimethyl sulfoxide (DMSO) (100 ml). The mixture was heated at 60° C. for 20 hours and then poured into 3% NaHCO3 solution and extracted with ethyl acetate. The organic layer was dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica gel (10% ethyl acetate in hexane) to give 4-cyanomethyl-1-diphenylmethylpiperidine (61.4%): mp 103°-104° C. and 3-(2-cyanoethyl)-1-diphenylmethyl pyrrolidine (20.9%):oil.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography on silica gel (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-26fdfabe7bc84f19a7cfb768fe51d43e
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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