Sodium Cyanide → 1-Benzhydryl-3-methylazetidine-3-carbonitrile

HRID 1461111Notes

Reaction equation

HRID 1461111 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH2:11][C:10]([CH3:17])(OS(C)(=O)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C-:24]#[N:25].[Na+]>CN(C)C=O>[C:24]([C:10]1([CH3:17])[CH2:11][N:8]([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:9]1)#[N:25]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 100652951-Benzhydryl-3-methylazetidin-3-yl methanesulfonate

Product 1

HCID 100840771-Benzhydryl-3-methylazetidine-3-carbonitrileYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

33.1 g (100 mmol) of 1-diphenylmethyl-3-methyl-3-methylsulphonyloxyazetidine are added to a suspension of sodium cyanide (11 g, 225 mmol) in dimethylformamide (90 ml) and the mixture is stirred at 65°-70° C. for 6 hours. It is cooled and poured onto a water/ice mixture, the product is filtered off, washed with water and dried at 50° C. and 21.75 g (83%) of 3-cyano-1-diphenylmethyl-3-methylazetidine, melting point 86°-88° C., are obtained.

Workup

  1. temperatureIt is cooled
  2. filtrationthe product is filtered off
  3. washwashed with water
  4. customdried at 50° C.

Sources & evidence

ORD record
ord-0dc926b8927648c29c249a1cb242f0b4
Source dataset
uspto-grants-1991_12
Patent number
US05073646

Reaction notes

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