Reaction #53937

ord-e2e0ee6db3284bfbb9078e69bf09e43f

Reaction equation

[Na+].[OH-]
NaOH
CN([C@H]1CC[C@H](O)CC1)S(=O)(=O)c1ccc(Br)cc1
trans-4-Bromo-N-(4-hydroxy-cyclohexyl)-N-methyl-benzenesulfonamide
CCN(CC)CCCl.Cl
2-diethylamino-ethylchlorid.hydrochloride
→
CCN(CC)CCO[C@H]1CC[C@H](N(C)S(=O)(=O)c2ccc(Br)cc2)CC1
trans-4-Bromo-N-[4-(2-diethylamino-ethoxy)-cyclohexyl]-N-methyl-benzenesulfonamide
Yield 84.9%

Reactants

[Na+].[OH-]
NaOH
CN([C@H]1CC[C@H](O)CC1)S(=O)(=O)c1ccc(Br)cc1
trans-4-Bromo-N-(4-hydroxy-cyclohexyl)-N-methyl-benzenesulfonamide
CCN(CC)CCCl.Cl
2-diethylamino-ethylchlorid.hydrochloride

Reagents

CCCC[N+](CCCC)(CCCC)CCCC.O=S(=O)([O-])O
Bu4NHSO4

Solvents

Cc1ccccc1
toluene

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherthe phases were separated
  2. 2
    Dryingthe organic phase dried over Na2SO4

Procedure

To 350 mg (1 mmol) trans-4-Bromo-N-(4-hydroxy-cyclohexyl)-N-methyl-benzenesulfonamide in 6 ml toluene was added 344 mg (2.0 mmol) 2-diethylamino-ethylchlorid.hydrochloride and a catalytic amount of Bu4NHSO4 followed by 4 ml 50% NaOH. The mixture was stirred at RT over night, the phases were separated and the organic phase dried over Na2SO4. Column chromatography on silica gel with CH2Cl2/MeOH 15:1 yielded 380 mg (84%) trans-4-Bromo-N-[4-(2-diethylamino-ethoxy)-cyclohexyl]-N-methyl-benzenesulfonamide as light yellow oil, MS: 447 (MH+, 1Br).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858651B2uspto-grants-2005_02