[(6-chloropyridin-3-yl)methyl]dimethylamine synthesis

Yield:221146-31-2 36%

Reaction Conditions:

with potassium carbonate in acetonitrile at 55; for 20 h;

Steps:

68 Example 68; (7R, 9aS)-trans-[6-(2-Benzo[d]isoxazol-3-yl-octahydro-pyrido[1,2-a]pyrazin-7-ylmethoxy)-pyridin-3-ylmethyl]-dimethyl-amine

To a SOLUTION OF 2-CHLORO-5-(CHLOROMETHYL) pyridine (509 mg, 3. 14 mmole) in 7 mL of dry acetonitrile is added 3. 14 mL (6. 28 MMOL) of A 2M solution of DIMETHYLAMINE in THF followed by 434 mg (3.14 MMOL) of potassium carbonate. The reaction is heated at 55 °C for 20 h. After cooling, the reaction mixture is quenched with 5 mL of water, extracted three- times with methylene chloride, and dried over sodium sulfate. Concentration of the solvent provided an oil which was purified by silica gel chromatography to provide 194 mg (36% yield) of 1- (6-CHLORO-PYRIDIN-3-YLMETHYL)-DIMETHYLAMINE. DIAGNOSTIC C13 NMR (100 MHZ, CDCI3) 45.5, 60.7, 124. 2, 133. 6, 139. 7, 150. 2, 150. 4; MS 173. 2 (M+H).

References:

WO2004/81007,2004,A1 Location in patent:Page 52