Ammonium Acetate → 4-Amino-1-benzyl-3,5-dimethyl-3-ethylpiperidine

HRID 1063340Notes

Reaction equation

HRID 1063340 reaction equation
C([O-])(=O)C.[NH4+].[CH2:6]([N:13]1[CH2:18][CH:17]([CH3:19])[C:16](=O)[C:15]([CH3:23])([CH2:21][CH3:22])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([BH3-])#[N:25].[Na+]>CO>[NH2:25][CH:16]1[CH:17]([CH3:19])[CH2:18][N:13]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:14][C:15]1([CH3:23])[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 222788971-Benzyl-3,5-dimethyl-3-ethyl-4-piperidone

Product 1

HCID 102145914-Amino-1-benzyl-3,5-dimethyl-3-ethylpiperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Ammonium acetate (2.5 g, 32.46 mmol) was added to the stirred solution of 1-benzyl-3,5-dimethyl-3-ethyl-4-piperidone (3.0 g, 12.25 mmol) in methanol (40 ml) and stirring was continued for 20 hr at ambient temperature. The resulting mixture was cooled at 0° C. and sodium cyanoborohydride (0.8 g, 12.7 mmol) was added to it. Cooling was removed after 10 min. and resulting mixture was stirred for 20 hr at ambient temperature. The reaction mixture was concentrated to dryness, triturated with water, acidified with conc. HCl (pH 2) and extracted with ethyl acetate to remove impurities. The aqueous layer was basified with 1M sodium hydroxide solution (pH 9) and extracted with ethyl acetate. Ethyl acetate extract was dried (Na2SO4) and concentrated to dryness to furnish 4-amino-1-benzyl-3,5-dimethyl-3-ethylpiperidine.

Workup

  1. temperatureCooling
  2. customwas removed after 10 min.
  3. customresulting mixture
  4. stirringwas stirred for 20 hr at ambient temperature
  5. concentrationThe reaction mixture was concentrated to dryness
  6. customtriturated with water
  7. extractionextracted with ethyl acetate
  8. customto remove impurities
  9. extractionextracted with ethyl acetate
  10. extractionEthyl acetate extract
  11. dry with materialwas dried (Na2SO4)
  12. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0153f59e88c942ed959ad76a15c21d6d
Source dataset
uspto-grants-2005_11
Patent number
US06964966B2

Reaction notes

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