Sodium Chloride → Mofegiline

HRID 376097Notes

Reaction equation

HRID 376097 reaction equation
C([N-:3][CH:4]=O)=O.[Na+].C(#N)C.ClC/[C:12](=[CH:22]/[F:23])/[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1.[Cl-].[Na+]>C1(C)C=CC=CC=1.O.CN(C)C=O>[NH2:3][CH2:4]/[C:12](=[CH:22]/[F:23])/[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 6342AcetonitrileHCID 9815806(E)-1-chloro-2-(fluoromethylene)-4-(p-fluorophenyl)butaneHCID 10877056Sodium Diformylamide

Product 1

HCID 6437850Mofegiline

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Combine sodium diformylamide (70 lb) and acetonitrile (903 lb). With agitation, add N,N-dimethylformamide (119 lb). Add a solution of (E)-1-chloro-2-(fluoromethylene)-4-(p-fluorophenyl)butane (126 lb) in toluene. Warm to 80° C. After 6 hours, add a 10% by weight solution of sodium chloride in water (1168 lb). Agitate for 15 minutes, separate the layers. Remove the organic layer to give the title compound as a solution in acetonitrile/N,N-dimethylformamide.

Workup

  1. customseparate the layers
  2. customRemove the organic layer

Sources & evidence

ORD record
ord-522700bca1c84d56a60c5c77989b64b8
Source dataset
uspto-grants-1996_01
Patent number
US05488188

Reaction notes

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