3,4-(Methylenedioxy)phenylacetonitrile → 2-(alpha-Cyano-3,4-methylenedioxybenzylidene)-1-methylpyrrolidine

HRID 1278070Notes

Reaction equation

HRID 1278070 reaction equation
[Na].[CH2:2]1[O:13][C:12]2[CH:11]=[CH:10][C:6]([CH2:7][C:8]#[N:9])=[CH:5][C:4]=2[O:3]1.CN(C)[C:16]1[CH2:20][CH2:19][CH2:18][N+:17]=1[CH3:21].COS([O-])(=O)=O>C(O)C>[C:8]([C:7](=[C:16]1[CH2:20][CH2:19][CH2:18][N:17]1[CH3:21])[C:6]1[CH:10]=[CH:11][C:12]2[O:13][CH2:2][O:3][C:4]=2[CH:5]=1)#[N:9]

Participants

5

Reactant 3

HCID 781783,4-(Methylenedioxy)phenylacetonitrileHCID 5360545SodiumHCID 1784830372-Dimethylamino-1-methyl-1-pyrrolinium methylsulfate

Product 1

HCID 541512022-(alpha-Cyano-3,4-methylenedioxybenzylidene)-1-methylpyrrolidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add (dropwise at 80°, with stirring) a solution of 3.5 g of sodium in 80 ml of ethanol to a mixture of 16.1 g of 3,4-methylenedioxybenzylcyanide and 36 g of 2-dimethylamino-1-methyl-1-pyrrolinium-methylsulfate. Continue boiling the resulting reaction mixture for a further 2 hours. Then distil off the solvent under a vacuum and take up the residue with water/diethyl ether. Collect the ethereal layer. Dry it over sodium sulfate and concentrate it to obtain 18 g (67% of theory) of the title compound as oily liquid.

Workup

  1. additionAdd (dropwise at 80°
  2. customthe resulting reaction mixture for a further 2 hours
  3. customThen distil off the solvent under a vacuum
  4. customCollect the ethereal layer
  5. dry with materialDry it over sodium sulfate
  6. concentrationconcentrate it

Sources & evidence

ORD record
ord-e4dd16b6213b467da7fe405c831f3ce1
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

Loading…