Triethylamine → 1,1-Dimethylethyl 4-[2-[[(methylsulfonyl)amino]methyl]phenyl]-1-piperazinecarboxylate
Reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][NH2:21])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl.CCOCC>[C:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][NH:21][S:30]([CH3:29])(=[O:32])=[O:31])[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
1-Boc-4-(2-aminomethyl-phenyl)-piperazine (2.09 g, 7.18 mmol) was dissolved in methylene chloride (50 mL), cooled to 0° C. and treated with triethylamine (1.5 mL, 10.8 mmol) followed by methanesulfonyl chloride (0.67 mL, 8.61 mmol). The resulting mixture was stirred for about 3 hours at r.t., and then diluted with ether (200 mL) and washed with water (50 mL), saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL), which is then dried over anhydrous magnesium sulfate. Concentration under reduced pressure followed by silica gel chromatography (30% ethyl acetate in hexanes) afforded the title compound (2.07 g, 78%) as a clear oil.
Workup
- washwashed with water (50 mL), saturated aqueous sodium bicarbonate (50 mL) and brine (50 mL), which
- dry with materialis then dried over anhydrous magnesium sulfate
- concentrationConcentration under reduced pressure
Sources & evidence
- ORD record
- ord-64b4835ac6564faf96cf8793a283771a
- Source dataset
- uspto-grants-2007_11
- Patent number
- US07291619B2
Reaction notes
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