Hydrazine → 3-(4-(4-Fluorophenyl)piperidin-1-yl)propan-1-amine

HRID 2269215Notes

Reaction equation

HRID 2269215 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16]C3C=CC=C4C(NC(=O)C=34)=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[NH2:28]N>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][NH2:28])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 227294733-[4-(4-Fluorophenyl)piperidin-1-yl]propylphthalimide

Product 1

HCID 101985993-(4-(4-Fluorophenyl)piperidin-1-yl)propan-1-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-[4-(4-fluorophenyl)piperidin-1-yl] propylphthalimide (4.5 g, 12.3 mmol) in methanol (200 mL) was added 4 ml of hydrazine and the mixture was refluxed for 8 h. It was cooled, and the white solid was filtered and washed with methanol (20 mL). Solvent was evaporated, and the residue was dried under vacuum for 4 h. Chloroform (50 mL) was added to this material, it was stirred for 1 h and filtered. The white solid was washed with more chloroform (20 mL), and the solvent was evaporated from the combined filtrates to leave the crude product as an oil. It was purified by column chromatography on silica gel using dichloromethane/methanol/2M ammonia in methanol (10/3/1) as the eluent.

Workup

  1. temperaturethe mixture was refluxed for 8 h
  2. temperatureIt was cooled
  3. filtrationthe white solid was filtered
  4. washwashed with methanol (20 mL)
  5. customSolvent was evaporated
  6. customthe residue was dried under vacuum for 4 h
  7. additionChloroform (50 mL) was added to this material, it
  8. filtrationfiltered
  9. washThe white solid was washed with more chloroform (20 mL)
  10. customthe solvent was evaporated from the combined filtrates

Sources & evidence

ORD record
ord-3ae03ed268aa4724ae9f05ab07554393
Source dataset
uspto-grants-2001_12
Patent number
US06329393B1

Reaction notes

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