Triethylamine → n-[(1-Boc-4-cyclohexyl-4-piperidyl)methyl]methanesulfonamide
Reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][C:11]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)([CH2:14][NH2:15])[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>[C:1]([N:8]1[CH2:9][CH2:10][C:11]([CH2:14][NH:15][S:30]([CH3:29])(=[O:32])=[O:31])([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:12][CH2:13]1)([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]Participants
Conditions
- Temperature
- 0 °C
Procedure
A 15-mL, round-bottomed flask was purged with nitrogen and then charged with the amine from Step A (0.063 g, 0.213 mmol), 1.7 mL of methylene chloride, and triethylamine (0.045 mL, 0.320 mmol). The reaction mixture was cooled at 0° C. in an ice-water bath and then methanesulfonyl chloride (0.018 mL, 0.23 mmol) was added dropwise via syringe. The resulting mixture was stirred at 0° C. for 50 min, warmed to room temperature, and stirred for 16.5 h. The reaction mixture was then diluted with methylene chloride and washed with two portions of 1N HCl solution, saturated sodium bicarbonate solution, water, and saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated. The crude product was purified by column chromatography (1:1 methylene chloride-acetone) to give the desired product (0.074 g) as a white solid.
Workup
- customA 15-mL, round-bottomed flask was purged with nitrogen
- temperaturewarmed to room temperature
- stirringstirred for 16.5 h
- washwashed with two portions of 1N HCl solution, saturated sodium bicarbonate solution, water, and saturated sodium chloride solution
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customThe crude product was purified by column chromatography (1:1 methylene chloride-acetone)
Sources & evidence
- ORD record
- ord-e72a06403d6b473880dcdc981204e608
- Source dataset
- uspto-grants-2002_02
- Patent number
- US06350760B1
Reaction notes
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