Water → Mofegiline

HRID 1489917Notes

Reaction equation

HRID 1489917 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-8f3903f462b1476ba63f6d8904e638fa
Source dataset
uspto-grants-1997_10
Patent number
US05679854

Reaction notes

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