Potassium Hydroxide → 3-({6-[(Piperidin-1-yl)methyl]pyridin-2-yl}oxy)propan-1-amine
Reaction equation
[N:1]1([CH2:7][C:8]2[N:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][NH:18]C=O)[CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+]>CO>[N:1]1([CH2:7][C:8]2[N:13]=[C:12]([O:14][CH2:15][CH2:16][CH2:17][NH2:18])[CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
N-[3-(6-Piperidinomethyl-2-pyridyloxy)propyl]formamide (19.6 g, 70.7 mmoles) [prepared in Step B] was added to a solution of 85% potassium hydroxide pellets (18.63 g, 0.332 mole) dissolved in 180 mL of methanol and the solution was heated at gentle reflux for 20 hours. The solvent was stripped in vacuum and the residue partially purified by redissolving in about 180 mL of 20% methanol-methylene chloride and passing through a pad of 38 g of silica gel. The silica was washed with an additional 120 mL of eluant and the combined filtrates were evaporated to an amber oil. Final purification was effected by flash chromatography on 120 g of silica gel (230-400 mesh) using a gradient elution of methanol-methylene chloride containing 0.5% NH40H. The title compound was obtained as a yellow oil in 63% yield.