N-Methylcyclohexylamine → 4-(bromomethyl)-N-cyclohexyl-N-methylbenzenesulfonamide

HRID 422585Notes

Reaction equation

HRID 422585 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.CCN(CC)CC.[CH3:20][NH:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1>C1COCC1.C(Cl)Cl>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:21]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[CH3:20])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 7514N-MethylcyclohexylamineHCID 8471TriethylamineHCID 27344094-(Bromomethyl)benzenesulfonyl chloride

Product 1

HCID 190232724-(bromomethyl)-N-cyclohexyl-N-methylbenzenesulfonamideYield 24.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The 4-(bromomethyl)benzene-1-sulfonyl chloride (1 g, 3.71 mmol), Et3N (0.776 mL, 5.56 mmol) and N-methylcyclohexylamine (0.42 g, 3.71 mmol) were reacted overnight in THF (6 mL) at ambient temperature. The mixture was diluted with DCM and washed with water. The organics were dried over MgSO4, filtered, concentrated and purified by chromatography on silica gel using an heptane/EtOAc gradient (100/0 to 50/50) to give the title compound (0.317 g, 24.6%): 1H NMR (CDCl3) δ 7.88-7.77 (d, 2H, J=8.4 Hz), 7.52 (d, 2H, J=8.4 Hz), 4.62 (s, 2H), 3.87-3.60 (m, 1H), 2.75 (s, 3H), 1.79-1.69 (m, 2H), 1.66-1.57 (m, 1H), 1.52-1.50 (m, 1H), 1.30 (m, 4H), 1.14-0.84 (m, 2H)

Workup

  1. washwashed with water
  2. dry with materialThe organics were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by chromatography on silica gel using an heptane/EtOAc gradient (100/0 to 50/50)

Sources & evidence

ORD record
ord-8586af3aba91441a8b77fb94bd51280d
Source dataset
uspto-grants-2012_01
Patent number
US08101645B2

Reaction notes

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