4-Chlorobenzyl cyanide → 2-(alpha-Cyano-4-chlorobenzylidene)-1-methylpyrrolidine

HRID 1278053Notes

Reaction equation

HRID 1278053 reaction equation
C(O[C:4]1(OCC)[CH2:8][CH2:7][CH2:6][N:5]1[CH3:9])C.[Cl:13][C:14]1[CH:22]=[CH:21][C:17]([CH2:18][C:19]#[N:20])=[CH:16][CH:15]=1>C1C=CC=CC=1>[C:19]([C:18](=[C:4]1[CH2:8][CH2:7][CH2:6][N:5]1[CH3:9])[C:17]1[CH:21]=[CH:22][C:14]([Cl:13])=[CH:15][CH:16]=1)#[N:20]

Participants

4

Reactant 2

HCID 2415824-Chlorobenzyl cyanideHCID 2973082,2-Diethoxy-1-methylpyrrolidine

Product 1

HCID 538671752-(alpha-Cyano-4-chlorobenzylidene)-1-methylpyrrolidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Boil 22.7 g of 2,2-diethoxy-1-methylpyrrolidine, 19.8 g of 4-chlorobenzylcyanide and 90 ml of benzene for 1 hour under reflux and with stirring. Distil off the volatile constituents under a vacuum. After trituration with a little diethyl ether, filter off the residue to obtain 20.8 g (68% of theory) and the title compound (m.p. 71° to 72° from isopropanol).

Workup

  1. customDistil off the volatile constituents under a vacuum
  2. filtrationAfter trituration with a little diethyl ether, filter off the residue
  3. customto obtain 20.8 g (68% of theory)

Sources & evidence

ORD record
ord-38d157ccb44247ad82d5a58cc7c67f0b
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

Loading…