Ammonium Acetate → 1-Benzyl-3,3-diMethyl-piperidin-4-aMine

HRID 1063295Notes

Reaction equation

HRID 1063295 reaction equation
C([O-])(=O)C.[NH4+].[CH2:6]([N:13]1[CH2:18][CH2:17][C:16](=O)[C:15]([CH3:21])([CH3:20])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([BH3-])#[N:23].[Na+]>CO>[NH2:23][CH:16]1[CH2:17][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([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 97944131-Benzyl-3,3-dimethylpiperidin-4-one

Product 1

HCID 102361061-Benzyl-3,3-diMethyl-piperidin-4-aMine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Ammonium acetate (3.5 g, 45.45 mmol) was added to the stirred solution of 1-benzyl-3,3-dimethyl-4-piperidone (2.0 g, 9.2 mmol), in methanol (20 ml) and stirring was continued for 3 hr at ambient temperature. The resulting mixture was cooled at 0° C. and sodium cyanoborohydride (0.58 g, 9.2 mmol) was added. Cooling was removed after 10 min. and resulting mixture was stirred for 6 hr at ambient temperature. The reaction mixture was concentrated to dryness, triturated with water, acidified with conc. HCl (pH 3˜4) and extracted with ethyl acetate to remove impurities. The aqueous layer was basified with 1 M sodium hydroxide solution (pH˜10) and extracted with ethyl acetate. Ethyl acetate extract was dried (Na2SO4) and concentrated to dryness to furnish 4-amino-1-benzyl-3,3-dimethyl piperidine. Yield 1.6 g (77%), C14H22N2, m/z 219 (M+1), PMR (CDCl3): 0.84 (s, 3H), 0.98 (s, 3H), 1.48 (bs, 2H, D2O exchangeable), 1.66 (m, 2H), 2.04 (m, 2H), 2.42 (m, 2H), 2.86 (m, 1H), 3.46 (dd, 2H), 7.32 (m, 5H).

Workup

  1. temperatureCooling
  2. customwas removed after 10 min.
  3. customresulting mixture
  4. stirringwas stirred for 6 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-95afe5e016d44813b6221005fe6bc30f
Source dataset
uspto-grants-2005_11
Patent number
US06964966B2

Reaction notes

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