Trifluoroacetic acid → 4-Fluoro-N-methyl-benzenepropanamine

HRID 1158142Notes

Reaction equation

HRID 1158142 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)C)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][CH2:9][NH:7][CH3:6])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59512610[3-(4-Fluoro-phenyl)-propyl]-methyl-carbamic acid tert-butyl ester

Product 1

HCID 110842664-Fluoro-N-methyl-benzenepropanamineYield 72.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-(4-fluoro-phenyl)-propyl]-methyl-carbamic acid tert-butyl ester (0.417 g, 1.560 mmol) in 3 mL of dichloromethane, was added trifluoroacetic acid (3 mL). After stirring at room temperature for 3 h, the reaction mixture was concentrated under reduced pressure. The residue was re-dissolved in 20 mL of ethyl acetate and the resulting solution was washed with NaOH solution (1N) and brine, and dried over anhydrous Na2SO4. Removal of the solvent under reduced pressure provided the title compound as a colorless oil (0.189 g, 72% yield), which was used directly in the next step (Step d of Specific Scheme 7) without further purification. GC-MS: tR=5.6 min; m/z 167 (M+).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was re-dissolved in 20 mL of ethyl acetate
  3. washthe resulting solution was washed with NaOH solution (1N) and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-7451f565c6c0429b8b8abb2b9fa91d62
Source dataset
uspto-grants-2010_10
Patent number
US07807720B2

Reaction notes

Loading…