1-[(2-methylphenyl)methyl]piperidin-4-one

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 1.73 g of 4-(2-keto-1-benzimidazolyl)piperidine and 1.54 g of N-(2-methylbenzyl)4-piperidone in 20 ml of MeOH was added 51 ml of 0.3M methanolic solution of ZnCl2—NaBH3CN at room temperature. The reaction mixture was stirred at room temperature for 4 h and quenched with saturated aqueous NaHCO3. The mixture was extracted with EtOAc, and the organic layer was washed with the 1:1 solution of saturated aqueous NaHCO3 and brine, and dried over anhydrous Na2SO4. The organic solvent was evaporated and recrystallization of the residue from EtOAc gave 1.78 g of the target compound as a colorless powder. quenched with saturated aqueous NaHCO3 The mixture was extracted with EtOAc the organic layer was washed with the 1:1 solution of saturated aqueous NaHCO3 and brine dried over anhydrous Na2SO4 The organic solvent was evaporated recrystallization of the residue from EtOAc

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 2.00 g of 4-piperidone monohydrate hydrochloride and 5.40 g of potassium carbonate in 30 ml of CH3CN was added dropwise 1.57 ml of 2-methyl benzyl bromide at 0° C. After stirred at 0° C. or 3.5 h, the mixture was stirred at room temperature for an hour. At 0° C., the mixture was quenched with water and extracted with CHCl3. The organic layer was washed with water, aqueous NaOH, and brine, and dried over anhydrous Na2SO4. The organic solvent was evaporated to give the crude product of 2.52 g of N-(2-methylbenzyl)-4-piperidone as a yellow oil. the mixture was stirred at room temperature for an hour At 0° C., the mixture was quenched with water extracted with CHCl3 The organic layer was washed with water, aqueous NaOH, and brine dried over anhydrous Na2SO4 The organic solvent was evaporated