Ethylamine hydrochloride → 1-Carbethoxy-4-ethylamino-3-methylpiperidine
Reaction equation
Cl.[CH2:2]([NH2:4])[CH3:3].[C:5]([N:10]1[CH2:15][CH2:14][C:13](=O)[CH:12]([CH3:17])[CH2:11]1)([O:7][CH2:8][CH3:9])=[O:6].[OH-].[K+].C([BH3-])#N.[Na+]>CO>[C:5]([N:10]1[CH2:15][CH2:14][CH:13]([NH:4][CH2:2][CH3:3])[CH:12]([CH3:17])[CH2:11]1)([O:7][CH2:8][CH3:9])=[O:6]Participants
Conditions
- Temperature
- 0 °C
Procedure
Ethylamine hydrochloride (5 g, 61.34 mmol) was added to the stirred solution of 1-carbethoxy-3-methyl-4-piperidone (3.5 g, 18.9 mmol) obtained as described in Preparation 1, in methanol (30 ml) followed by 3.43 g (61.34 mmol) KOH. Stirring was continued for 3 hr at ambient temperature. The resulting mixture was cooled at 0° C. and sodium cyanoborohydride (1.4 g, 22.22 mmol) was added to it. Cooling was removed after 10 min. and resulting mixture was stirred for 16 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 give 1-carbethoxy-4-ethylamino-3-methylpiperidine. Yield 2.3 g (54%), C11H22N2O2, m/z 215 (M+1).
Workup
- customobtained
- temperatureCooling
- customwas removed after 10 min.
- customresulting mixture
- stirringwas stirred for 16 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-f4fec2eaadf041a4af7fd5112811f650
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07626032B2
Reaction notes
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