Water → Mofegiline

HRID 376095Notes

Reaction equation

HRID 376095 reaction equation
C(Cl)(=O)C(Cl)=O.C[N:8]([CH3:11])C=O.[F:12]/[CH:13]=[C:14](\[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)/CO.O>C1(C)C=CC=CC=1>[NH2:8][CH2:11]/[C:14](=[CH:13]/[F:12])/[CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 10943450(E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol

Product 1

HCID 6437850Mofegiline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-5 °C

Procedure

Combine oxalyl chloride (25.2 g, 0.198 mol) and toluene (200 mL). Cool to -5° C. Add N,N-dimethylformamide (15.0 g, 0.21 mol) as a solution in toluene (20 mL). Warm to 25° C. After 30 minutes, add a solution of (E)-2-(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol (24.7 g, 30% by weight in toluene, 0.124 mol). After 18 hours, add water (500 mL) and stir for 30 minutes. Separate the organic layer, dry over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. temperatureWarm to 25° C
  2. waitAfter 18 hours
  3. customSeparate the organic layer
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. customevaporate in vacuo

Sources & evidence

ORD record
ord-0e0601195cd24b1c8b1d925c720d7e13
Source dataset
uspto-grants-1996_01
Patent number
US05488188

Reaction notes

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