Sodium hydride → 5-Piperidin-1-ylmethyl-2-(3-piperidin-1-yl-propoxy)-pyridine
Reaction equation
[H-].[Na+].[N:3]1([CH2:9][CH2:10][CH2:11][OH:12])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.Br[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:16][N:15]=1>CN(C=O)C>[N:21]1([CH2:20][C:17]2[CH:18]=[CH:19][C:14]([O:12][CH2:11][CH2:10][CH2:9][N:3]3[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]3)=[N:15][CH:16]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1Participants
5
Procedure
To a suspension of NaH (1.5 mmol) in DMF is added 3-piperidin-1-yl-propan-1-ol (1.1 mmol). After 30 min, 2-bromo-5-piperidin-1-ylmethyl-pyridine (1 mmol) is added to the mixture. After 18 h, the reaction is extracted with ethyl acetate (100 mL) and washed with 1 N NaHCO3 (50 mL) and H2O(3×50 mL). The organic layer is dried, concentrated, and chromatographed on SiO2 to provide the title compound.