Methyl iodide → N-methyl-N-[(1-Boc-4-cyclohexyl-4-piperidyl)methyl]methane sulfonamide

HRID 1700261Notes

Reaction equation

HRID 1700261 reaction equation
[H-].[Na+].[C:3]([N:10]1[CH2:15][CH2:14][C:13]([CH2:22][NH:23][S:24]([CH3:27])(=[O:26])=[O:25])([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:12][CH2:11]1)([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[CH3:28]I>CN(C)C=O.C(OCC)(=O)C>[CH3:28][N:23]([CH2:22][C:13]1([CH:16]2[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:12][CH2:11][N:10]([C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])[CH2:15][CH2:14]1)[S:24]([CH3:27])(=[O:26])=[O:25]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18318091n-[(1-Boc-4-cyclohexyl-4-piperidyl)methyl]methanesulfonamide

Product 1

HCID 18318104N-methyl-N-[(1-Boc-4-cyclohexyl-4-piperidyl)methyl]methane sulfonamideYield 72.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A 10-mL, round-bottomed flask was purged with nitrogen and then charged with a 60% sodium hydride dispersion in mineral oil (0.005 g, 0.125 mmol), and the flask was cooled at 0° C. in an ice-water bath. A solution of the sulfonamide from Step B (0.040 g, 0.107 mmol) in 0.8 mL of dimethylformamide was then added dropwise via syringe. The resulting mixture was stirred at 0° C. for 17 min, warmed to room temperature, and stirred for 10 min. The resulting thick mixture was then charged with methyl iodide (0.033 mL, 0.535 mmol), and the clear mixture was then stirred at room temperature for 5 days. The reaction mixture was then diluted with ethyl acetate and washed with two portions of 1 N HCl solution, saturated sodium bicarbonate solution, water, and saturated sodium chloride solution, dried over sodium sulfate, filtered, and concentrated to give the title compound (0.030 g) as a light yellow oil.

Workup

  1. customA 10-mL, round-bottomed flask was purged with nitrogen
  2. temperaturewarmed to room temperature
  3. stirringstirred for 10 min
  4. stirringthe clear mixture was then stirred at room temperature for 5 days
  5. washwashed with two portions of 1 N HCl solution, saturated sodium bicarbonate solution, water, and saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5b7a518edf3a45489ab4ebdda2d7a187
Source dataset
uspto-grants-2002_02
Patent number
US06350760B1

Reaction notes

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