Morpholine → HCID 72188144, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-N-[(4-chlorophenyl)-methyl]-2,6-diethyl-benzamide (0.34 g, 0.90 mmol) in toluene (3 ml), morpholine (0.11 g, 1.29 mmol), caesium carbonate (0.40 g, 1.22 mmol) and 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.06 g, 0.09 mmol) are added. After degassing with argon for 30 min tris(dibenzylideneacetone)-dipalladium(0) (0.04 g, 0.04 mmol) are added and the mixture is heated at 120° C. for 16 h. After completion of the reaction (monitored by TLC) the mixture is filtered through a pad of celite and diluted with ethyl acetate (30 ml), the organic layer is washed with water and dried over sodium sulfate and concentrated in vacuo. The resulting crude product is purified by preparative HPLC to obtain the N-[(4-chlorophenyl)-methyl]-2,6-diethyl-4-morpholin-4-yl-benzamide (example 41) (0.18 g, 0.47 mmol, 26%). [M+H]+ 387.2.

Provenance & Evidence