Sodium sulfate decahydrate → 3-(4-Fluorophenyl)-N-propylpropan-1-amine

HRID 1592330Notes

Reaction equation

HRID 1592330 reaction equation
[CH:1]1([NH:4][C:5](=O)[CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[CH2:3][CH2:2]1.[Li].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH:1]1([NH:4][CH2:5][CH2:6][CH2:7][C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)[CH2:2][CH2:3]1.[CH2:1]([NH:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=1)[CH2:2][CH3:3]

Participants

6

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 3028194LithiumHCID 56923282N-cyclopropyl-3-(4-fluorophenyl)propanamide

Product 2

HCID 469064523-(4-Fluorophenyl)-N-propylpropan-1-amineHCID 62529028N-cyclopropyl-3-(4-fluorophenyl)propylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of N-cyclopropyl-3-(4-fluorophenyl)propionamide (4.3 g, 20.8 mmoles) in 30 mL of dry tetrahydrofuran at 0° C. was added 1 equivalent of lithium aluminumhydride in tetrahydrofuran dropwise, and the mixture was refluxed for 2 hours. After cooling to room temperature was added sodium sulfate decahydrate slowly and the mixture was stirred for 0.5 hours. It was filtered through a plug of Celite® and evaporated to give an oily residue. It was purified by clolumn chromatography on silica gel with elution by 6:94 methanol-methylene chloride followed by 0.6:5.4:94 cNH4OH-methanol-methylene chloride to give 1.4 g of N-cyclopropyl-3-(4-fluorophenyl)propylamine and 1 g of N-propyl-3-(4-fluorophenyl)propylamine.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. filtrationIt was filtered through a plug of Celite®
  3. customevaporated
  4. customto give an oily residue
  5. customIt was purified by clolumn chromatography on silica gel with elution by 6:94 methanol-methylene chloride

Sources & evidence

ORD record
ord-04abd00da34747508bae973f0567f181
Source dataset
uspto-grants-2007_11
Patent number
US07291744B2

Reaction notes

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