Ammonium Acetate → HCID 10125064, compound
Reaction equation
C([O-])(=O)C.[NH4+].[CH3:6][C:7]1([CH3:15])[C:12](=O)[CH:11]([CH3:14])[CH2:10][NH:9][CH2:8]1.C([BH3-])#[N:17].[Na+]>CO>[NH2:17][CH:12]1[CH:11]([CH3:14])[CH2:10][NH:9][CH2:8][C:7]1([CH3:15])[CH3:6]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 3,3,5-trimethyl-4-piperidone (0.8 g, 5.67 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 (0.25 g, 3.96 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 (pH 10) and extracted with ethyl acetate. Ethyl acetate extract was dried (Na2SO4) and concentrated to dryness to furnish 4-amino-3,3,5-trimethylpiperidine. Yield 0.45 g (54%), C8H18N2, m/z 143 (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-f313d930de7c4e6799b441bc0a95e75c
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07393957B2
Reaction notes
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