Ammonium Acetate → HCID 10171448, compound
Reaction equation
C([O-])(=O)C.[NH4+].[CH2:6]([N:13]1[CH2:18][CH:17]([CH2:19][CH3:20])[C:16](=O)[CH:15]([CH2:22][CH3:23])[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]([CH2:19][CH3:20])[CH2:18][N:13]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:14][CH:15]1[CH2:22][CH3:23]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Ammonium acetate (10 g, 130 mmol) was added to the stirred solution of 1-benzyl-3,5-diethyl-4-piperidone (3.5 g, 14.3 mmol) in methanol (50 ml) and stirring was continued for 4 hr at ambient temperature. The resulting mixture was cooled at 0° C. and sodium cyanoborohydride (0.45 g, 7.14 mmol) was added to it. Cooling was removed after 10 min. and resulting mixture was stirred for 10 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 10) and extracted with ethyl acetate. Ethyl acetate extract was dried (Na2SO4) and concentrated to dryness to furnish 4-amino-1-benzyl-3,5-diethylpiperidine. Yield 3.4 g (97%), C16H26N2, m/z 247 (M+1).
Workup
- temperatureCooling
- customwas removed after 10 min.
- customresulting mixture
- stirringwas stirred for 10 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-42799c55bdf14a82811651a4258d0435
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07393957B2
Reaction notes
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