Sodium Chloride → Mofegiline

HRID 376094Notes

Reaction equation

HRID 376094 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.[Cl-].[Na+]>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 5234Sodium ChlorideHCID 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
0 °C

Procedure

Combine oxalyl chloride (2.71 g, 21.4 mmol) and toluene (20 mL). Cool to 0° C. Add N,N-dimethylformamide (1.62 g, 22.2 mmol) as a solution in toluene (2 mL). Warm to ambient temperature. After 10 minutes, cool to 0° C. Add (E)-2(fluoromethylene)-4-(p-fluorophenyl)butan-1-ol (4.0 g, 20.2 mmol) Warm to ambient temperature. After 18 hours, pour the reaction mixture into a saturated sodium chloride solution (100 mL). Extract the aqueous layer 3 times with toluene. Dry the combined organic layers over Na2SO4, filter, and evaporate in vacuo to give the title compound. 1H NMR (CDCl3, 300 MHz) δ2.52 (m, 2H), 2.75 (m, 2H), 3.91 (d, J=6 Hz, 2H), 6.65 (d, J=82.5 Hz, 1H), 6.95 (m, 2H), 7.15 (m, 2H).

Workup

  1. temperatureWarm to ambient temperature
  2. temperaturecool to 0° C
  3. waitAfter 18 hours
  4. extractionExtract the aqueous layer 3 times with toluene
  5. dry with materialDry the combined organic layers over Na2SO4
  6. filtrationfilter
  7. customevaporate in vacuo

Sources & evidence

ORD record
ord-7532d29c0b4a4da8b695594911c476fb
Source dataset
uspto-grants-1996_01
Patent number
US05488188

Reaction notes

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