Triethylamine → 4-[3-(2-Ethylhexanoylamino)propylthio]pyridine hydrochloride
Reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1.C(N(CC)CC)C.[CH2:21]([CH:23]([CH2:27][CH2:28][CH2:29][CH3:30])[C:24]([Cl:26])=[O:25])[CH3:22]>C(Cl)Cl>[ClH:26].[CH2:21]([CH:23]([CH2:27][CH2:28][CH2:29][CH3:30])[C:24]([NH:3][CH2:4][CH2:5][CH2:6][S:7][C:8]1[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=1)=[O:25])[CH3:22]Participants
5
Procedure
To a solution of 800 mg (3.32 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.22 ml (15.9 mmol) of triethylamine in 30 ml of methylene chloride was added 0.69 ml (3.98 mmol) of 2-ethylhexanoyl chloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water and dried. The solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 1.02 g of the desired compound (free base) (quant., pale yellow oil).
Workup
- temperaturecooling
- stirringthe mixture was stirred at room temperature for 30 minutes
- washThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water
- customdried
- distillationThe solvent was distilled off
- customThe residue was purified by column chromatography (eluent: ethyl acetate)
Sources & evidence
- ORD record
- ord-7cd1174c705b4e80a447e869ca6e581e
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05561147
Reaction notes
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