Potassium Iodide → HCID 19909642, compound

Reaction equation

N1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7]CCCl.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.[I-].[K+].[CH3:25][N:26]([CH3:29])C=O>>[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[CH2:18][CH2:19][N:20]([CH2:6][CH2:5][CH2:4][C:3]2[CH:25]=[N:26][CH:29]=[CH:7][CH:2]=2)[CH2:21][CH2:22]1

Participants

Reactant 4

HCID 4875Potassium Iodide

HCID 6228Dimethylformamide

HCID 944591-(2-Pyridyl)piperazine

HCID 1791132-(3-Chloro-propyl)-pyridine

Product 1

HCID 19909642HCID 19909642, compound

Conditions

Temperature: 80 °C

Procedure

A solution of 3-pyridinylpropylchloride (Example A) (3.0 g, 0.0193 mol), 1-(2-pyridinyl)piperazine (3.15 g, 0.0193 mol), potassium iodide (0.8 g, 0.005 mol) is dissolved in N,N-dimethylformamide (80 mL) and heated to 80° C. for 12 hours. The reaction is cooled and the precipitate is filtered. The filtrate is washed with sodium carbonate and extracted with dichloromethane. The organic layer is evaporated in vacuo and the residue is purified by column chromatography (silica gel, 10% ethanol/ethyl acetate). The major product is taken up in diethyl ether and the precipitate is filtered. The filtrate is evaporated in vacuo to give 0.8 g of 1-(2-pyridinyl)-4-[3-(3-pyridinyl)propyl]piperazine as a white solid; mp 51-52° C.