Ammonium Acetate → 4-Amino-1-carbethoxy-3,5-dimethylpiperidine
Reaction equation
C([O-])(=O)C.[NH4+].[C:6]([N:11]1[CH2:16][CH:15]([CH3:17])[C:14](=O)[CH:13]([CH3:19])[CH2:12]1)([O:8][CH2:9][CH3:10])=[O:7].C([BH3-])#[N:21].[Na+]>CO>[NH2:21][CH:14]1[CH:15]([CH3:17])[CH2:16][N:11]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:12][CH:13]1[CH3:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Ammonium acetate (20 g) was added to the stirred solution of 1-carbethoxy-3,5-dimethyl-4-piperidinone (4.5 g, 22.5 mmol) in methanol (200 ml) and stirred for 3 hr. The resulting mixture was cooled at 0° C. and sodium cyanoborohydride (1.4 g, 22.5 mmol) was added to it. Cooling was removed and stirring was for 3 hr at 35° C. The reaction mixture was concentrated, 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 give 4-amino-1-carbethoxy-3,5-dimethylpiperidine. The obtained 4-amino-1-carbethoxy-3,5-dimethylpiperidine was subjected to silica gel column chromatography. Elution with 5% methanol in chloroform furnished a solid, which was a mixture of stereoisomers, conformational analysis of which was not obtained.
Workup
- temperatureCooling
- customwas removed
- stirringstirring
- waitwas for 3 hr at 35° C
- concentrationThe reaction mixture was concentrated
- customtriturated with water
- extractionextracted with ethyl acetate
- customto remove impurities
- extractionextracted with ethyl acetate
- extractionEthyl acetate extract
- dry with materialwas dried (Na2SO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c26197da6db34554b6f0bc191d5c87a3
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07626032B2
Reaction notes
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