Dichloromethane → 4-(3-(N-2-pyridylmethylamino)propylthio]pyridine
Reaction equation
O[CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.C(Cl)Cl.CS(Cl)(=O)=O.[NH2:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1>>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[CH2:28][NH:27][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1Participants
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 5.26 g (31.1 mmol) of 4-(3-hydroxypropylthio)pyridine and 5.20 ml (37.3 mmol) of triethylamine in150 ml of methylene chloride, 2.90 ml (37.3 mmol) of methanesulfonyl chloride was added under ice-cooling with stirring. The mixture was stirred at room temperature for 30 minutes. The reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water and dried, and then the solvent was distilled off. To 6.33 g of the residue was added 2.64 ml (25.6 mmol) of 2-aminomethylpyridine. The resulting mixture was heated at 80° C. for 3 hours. After cooling, the mixture was purified by column chromatography (eluent: chloroform/methanol=25:1) to obtain 1.62 g of the desired compound (yield: 25.4%, yellow oil).
Workup
- temperaturecooling
- stirringThe mixture was stirred at room temperature for 30 minutes
- washThe reaction mixture was washed with a saturated aqueous solution of sodium bicarbonate and water
- customdried
- distillationthe solvent was distilled off
- temperatureAfter cooling
- customthe mixture was purified by column chromatography (eluent: chloroform/methanol=25:1)
Sources & evidence
- ORD record
- ord-07994ce1ab874ddab964fc999d5681da
- Source dataset
- uspto-grants-1996_10
- Patent number
- US05561147
Reaction notes
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