Reaction #1726729

Reaction equation

N-(3,3-diphenylpropyl)-N-(4-piperidinyl)-N′-[3-(trifluoromethyl)phenyl]urea

Phenylisocyanate

→

yellow oil

Yield 40.0%

4-((3,3-diphenylpropyl){[3-(trifluoromethyl)anilino]carbonyl}amino)-N-phenyl-1-piperidine carboxamide

Yield 40.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.WAITthe reaction is again agitated overnight
2. 2
   FiltrationThe resin is filtered
3. 3
   Washrinsed with dichloromethane
4. 4
   Concentrationthe filtrate is concentrated
5. 5
   OtherThe oil obtained
6. 6
   Washeluting with an equimolar mixture of heptane and ethyl acetate in order

Procedure

N-(3,3-diphenylpropyl)-N-(4-piperidinyl)-N′-[3-(trifluoromethyl)phenyl]urea (24 mg, 0.05 mmol) is dissolved in dichloromethane. Phenylisocyanate (9 mg, 0.075 mmol, 1.5 eq.) is added and the mixture is agitated for 2.5 hours. The aminomethyl resin (0.02 mmol) is added and the reaction is again agitated overnight. The resin is filtered, rinsed with dichloromethane and the filtrate is concentrated. The oil obtained is passed through a silica gel cartridge eluting with an equimolar mixture of heptane and ethyl acetate in order to obtain 12 mg (yield=40%) of a yellow oil after concentration.

Source