Methanol → HCID 22337580, compound

HRID 1644882Notes

Reaction equation

HRID 1644882 reaction equation
N([CH:4]([NH2:16])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[C:7]([F:15])[CH:6]=1)=[N+]=[N-].[CH3:17]O>>[F:15][C:7]1[CH:6]=[C:5]([CH:4]([NH2:16])[CH3:17])[CH:10]=[CH:9][C:8]=1[C:11]([F:12])([F:13])[F:14]

Participants

3

Reactant 2

HCID 887MethanolHCID 86637938HCID 86637938, compound

Product 1

HCID 22337580HCID 22337580, compoundYield 34%

Procedure

C-Azido-C-(3-fluoro-4-trifluoromethyl-phenyl)-methylamine (0.4 g) was dissolved in methanol (6 mL). The flask was evacuated and filled with nitrogen atmosphere before catalytic amount of Pd/C was added to the flask. The reaction was put under hydrogen atmosphere and stirred at r.t. over night. The flask was evacuated and filled with nitrogen before the reaction mixture was filtered through a celite pad. The solvent was removed and the crude product was purified on a colon (silica, CH2Cl2 followed by CH2Cl2/MeOH, 9:1) yielding 120 mg (34%) of 1-(3-Fluoro-4-trifluoromethyl-phenyl)-ethylamine. 1H NMR δ (CDCl3): 1.42 (3H, d), 4.22 (1H, q), 7.21-7.30 (m, 2H), 7.58 (1H, t).

Workup

  1. customThe flask was evacuated
  2. additionfilled with nitrogen atmosphere before catalytic amount of Pd/C
  3. additionwas added to the flask
  4. customThe flask was evacuated
  5. additionfilled with nitrogen before the reaction mixture
  6. filtrationwas filtered through a celite pad
  7. customThe solvent was removed
  8. customthe crude product was purified on a colon (silica, CH2Cl2 followed by CH2Cl2/MeOH, 9:1)

Sources & evidence

ORD record
ord-73a5b76b2754462d888ad81b143e6121
Source dataset
uspto-grants-2012_02
Patent number
US08124634B2

Reaction notes

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