Sodium Cyanide → 4-Benzyl-2-morpholineacetonitrile

HRID 372087Notes

Reaction equation

HRID 372087 reaction equation
[C-:1]#[N:2].[Na+].[CH2:4]([N:11]1[CH2:16][CH2:15][O:14][CH:13]([CH2:17]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CS(C)=O.O>[CH2:4]([N:11]1[CH2:16][CH2:15][O:14][CH:13]([CH2:17][C:1]#[N:2])[CH2:12]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 122977674-Benzyl-2-toluene-p-sulphonyloxymethylmorpholine

Product 1

HCID 32484164-Benzyl-2-morpholineacetonitrile

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

The mixture of finely ground sodium cyanide (39.6 g.) and 4-benzyl-2-(toluene-p-sulphonyloxymethyl)morpholine (144.4 g.) in dimethyl sulphoxide (600 ml.) is stirred and heated at 60°-65° C. for 3.5 hours. The mixture is cooled, diluted with water (6 1.) and extracted with ether (3 × 2 1.). The ether extracts are combined and washed with brine (2 × `1.) and dried over anhydrous magnesium sulphate and the solvent removed by evaporation in vacuo. The residue is recrystallised from petroleum ether (b.p. 40°-60° C.) to give 4-benzyl-2-cyanomethylmorpholine, m.p. 62° C.

Workup

  1. temperatureheated at 60°-65° C. for 3.5 hours
  2. temperatureThe mixture is cooled
  3. extractionextracted with ether (3 × 2 1.)
  4. washwashed with brine (2 × `1
  5. dry with material) and dried over anhydrous magnesium sulphate
  6. customthe solvent removed by evaporation in vacuo
  7. customThe residue is recrystallised from petroleum ether (b.p. 40°-60° C.)

Sources & evidence

ORD record
ord-14fd569274af490d9db41a92cf7ea9c1
Source dataset
uspto-grants-1978_05
Patent number
US04088814

Reaction notes

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