Hydrochloric Acid → 1-(3-Chlorophenyl)butan-1-amine

HRID 659977Notes

Reaction equation

HRID 659977 reaction equation
F[C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][CH2:10][CH3:11])[CH:5]=[CH:6][CH:7]=1.C([O-])(=O)C.[NH4+:17].C([BH3-])#N.[Na+].[ClH:22]>CO>[Cl:22][C:2]1[CH:3]=[C:4]([CH:8]([NH2:17])[CH2:9][CH2:10][CH3:11])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 204362041-(3-Fluorophenyl)butan-1-one

Product 1

HCID 588532391-(3-Chlorophenyl)butan-1-amineYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(3-fluorophenyl)butan-1-one (430 mg, 2.4 mmol) and ammonium acetate (1.09 g, 14.1 mmol) in methanol (10 mL) under nitrogen was added sodium cyanoborohydride (2.35 ml, 1M solution in THF, 2.35 mmol). The solution was stirred at room temperature for 38 h. after which time conc. HCl was added to give a pH˜2. After bubbling had ceased the solvent was removed under reduced pressure and the residue dissolved in ethyl acetate and water. The organic phase was collected and the aqueous phase washed with ethyl acetate (20 mL). The aqueous phase was basified to pH˜10 with solid KOH and the product extracted into ethyl acetate (3×20 mL). The organic layers were combined, washed with brine, dried (Na2SO4) and concentrated to give a pure product (120 mg, 28%).

Workup

  1. additionwas added
  2. customto give a pH˜2
  3. customAfter bubbling
  4. customwas removed under reduced pressure
  5. dissolutionthe residue dissolved in ethyl acetate
  6. customThe organic phase was collected
  7. washthe aqueous phase washed with ethyl acetate (20 mL)
  8. extractionthe product extracted into ethyl acetate (3×20 mL)
  9. washwashed with brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-526cc426781647b0b7e89589d9dc8680
Source dataset
uspto-grants-2011_12
Patent number
US08084456B2

Reaction notes

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