Reaction #52014

Reaction equation

Intermediate ( 4 )

N-benzyl-N′-[3,5-bis(trifluoromethyl)benzoyl]-N-{[4-(hydroxymethyl)cyclohexyl]methyl}sulfamide

2,6-di-t-butyl pyridine

iodopentane

→

title compound

Yield 73.9%

N-benzyl-N′-[3,5-bis(trifluoromethyl)benzoyl]-N-({4-[(pentyloxy)methyl]cyclohexyl}methyl)sulfamide

Yield 73.9%

Solvents

dichloromethane

Conditions

Workup

1. 1
   OtherAfter 45 minutes the reaction mixture was directly purified

Procedure

Intermediate (4) (27.6 mg, 50 μmole, 1.0 eq) was dissolved in dichloromethane (250 μL), after which 2,6-di-t-butyl pyridine (36 μL, 160 μmole, 3.2 eq), silver triflate (38.5 mg, 150 μmole, 3.0 eq) and iodopentane (23 μL, 175 μmole, 3.5 eq) were added. After 45 minutes the reaction mixture was directly purified to give 23 mg of the title compound. 1H NMR (500 MHz, DMSO-d6): δ 8.45 (s, 2H), 8.15 (s, 1H), 7.36 (d, 2H), 7.24 (t, 2H), 7.17 (t, 1H), 4.39 (s, 2H), 3.30 (water), 3.23 (t, 2H), 3.01 (d, 2H), 2.92 (d, 2H), 2.48 (DMSO), 1.61 (m, 2H), 1.54 (m, 2H), 1.41 (m, 2H), 1.34-1.19 (m, 6H), 0.82 (t, 3H), 0.62 (m, 4H).

Source