Dimethylformamide → N-Benzyl-3-cyanoazetidine

HRID 980771Notes

Reaction equation

HRID 980771 reaction equation
[CH2:1]([N:8]1[CH2:11][CH:10](O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[Na+].[CH3:16][N:17](C)C=O>O>[CH2:1]([N:8]1[CH2:11][CH:10]([C:16]#[N:17])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 38013451-benzylazetidin-3-ol

Product 1

HCID 19814762N-Benzyl-3-cyanoazetidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.7 g of 2A, and 1.2 g of sodium cyanide were stirred together in 1 ml of water and 20 ml of dimethylformamide at 60° C. for 16 hours. The solvent was evaporated under reduced pressure and the residue was purified by chromatography on silica gel using isopropanol in dichloromethane as eluent to give 1-benzyl-3-cyanoazetidine (2B), yield 0.5 g.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-7ae90c1b65b04bb7a0bfde3d3cde9f52
Source dataset
uspto-grants-1987_01
Patent number
US04639334

Reaction notes

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