Ammonium Acetate → 4-Amino-1-benzyl-3-ethyl-3-methylpiperidine
Reaction equation
C([O-])(=O)C.[NH4+].[CH2:6]([N:13]1[CH2:18][CH2:17][C:16](=O)[C:15]([CH2:21][CH3:22])([CH3:20])[CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([BH3-])#[N:24].[Na+]>CO>[NH2:24][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([CH2:21][CH3:22])[CH3:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Ammonium acetate (2.5 g, 32.46 mmol) was added to the stirred solution of 1-benzyl-3-ethyl-3-methyl-4-piperidinone (0.9 g, 3.9 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 (0.2 g, 3.1 mmol) was added to it. 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 (pH10) and extracted with ethyl acetate. Ethyl acetate extract was dried (Na2SO4) and concentrated to dryness to furnish 4-amino-1-benzyl-3-ethyl-3-methylpiperidine. Yield 0.6 g (66%), C15H24N2, m/z 233 (M+1).
Workup
- temperatureCooling
- customwas removed after 10 min.
- customresulting mixture
- stirringwas stirred for 6 hr at ambient temperature
- concentrationThe reaction mixture was concentrated to dryness
- customtriturated with water
- extractionextracted with ethyl acetate
- customto remove impurities
- extractionextracted with ethyl acetate
- extractionEthyl acetate extract
- dry with materialwas dried (Na2SO4)
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-02c863b1f2d3444096f4e52dcb329f3e
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07626032B2
Reaction notes
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