Reacción #78338

Ecuación de reacción

hydrogen chloride

4-(acryloyl-N-methylamino)-4-phenylpiperidine hydrochloride

compound

1-Benzoyl-3-(3,4-dichlorophenyl)-3-[3-[4-(pyrrolidin-1-ylcarbonyl)piperid-1-yl]propyl]piperidine Hydrochloride

K2CO3

→

expected product

Rendimiento 80.5%

3-[3-[4-(Acryloyl-N-methylamino)-4-phenylpiperid-1-yl]propyl]-1-benzoyl-3-(3,4-dichlorophenyl)piperidine Hydrochloride

Rendimiento 80.5%

Disolventes

DCM

water

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with AcOEt
2. 2
   Lavadothe organic phase is washed with water and with saturated NaCl solution
3. 3
   Secadodried over MgSO4
4. 4
   Otrothe solvent is evaporated off under vacuum
5. 5
   OtroThe residue is chromatographed on silica using a gradient of a DCM/MeOH mixture (99/1; v/v to 95/5; v/v) as the eluent
6. 6
   OtroThe product obtained
7. 7
   Otrothe precipitate formed
8. 8
   Filtraciónis filtered off

Procedimiento

A mixture of 0.27 g of 4-(acryloyl-N-methylamino)-4-phenylpiperidine hydrochloride, 0.45 g of the compound obtained in step B of EXAMPLE 1 and 0.3 g of K2CO3 in 3 ml of DMF is heated at 80° C. for 2 hours. The reaction mixture is poured into water and extracted with AcOEt, the organic phase is washed with water and with saturated NaCl solution and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a gradient of a DCM/MeOH mixture (99/1; v/v to 95/5; v/v) as the eluent. The product obtained is dissolved in DCM and acidified by the addition of ethereal hydrogen chloride and the precipitate formed is filtered off to give 0.2 g of the expected product, m.p.=128° C.

Fuente