Réaction #1075868

Équation de réaction

sodium cyanoborohydride

5-chloro-N-(5-methylpyridin-2-yl)-2-[(4-piperidinylmethyl)amino]benzamide

cyclopentanone

→

title compound

Rendement 58.1%

5-Chloro-N-(5-methylpyridin-2-yl)-2-[(1-cyclopentylpiperidin-4-yl)methylamino]benzamide

Rendement 58.1%

Solvants

tetrahydrofuran

methanol acetic acid

Conditions de réaction

Traitement

1. 1
   Concentrationthe mixture was concentrated in vacuo
2. 2
   LavageElution with 9:1 dichloromethane-2 M ammonia in methanol

Mode opératoire

A solution of 5-chloro-N-(5-methylpyridin-2-yl)-2-[(4-piperidinylmethyl)amino]benzamide from Example 99-A (0.45 g, 1.25 mmol) in 10 mL of 95:5 methanol-acetic acid was treated with excess cyclopentanone (1.11 mL, 12.5 mmol), followed by sodium cyanoborohydride (5.0 ml of a 1 M solution in tetrahydrofuran, 6.0 mmol). After stirring at 50° C. for 36 h, the mixture was concentrated in vacuo; and the residue was subjected to silica gel chromatography. Elution with 9:1 dichloromethane-2 M ammonia in methanol afforded 0.31 g (58%) of the title compound as a yellow solid.

Source