2-(4,ALPHA-DICHLOROBENZYL)PYRIDINE

In a 300 ml recovery flask, 10 g (42 mmol) of 2- [chloro (4-chlorophenyl) methyl] pyridine, (4-hydroxy) -4-piperidinobutanoic acid ethyl ester 9.9 g (42 mmol), And 100 ml of dimethylsulfoxide was added and 4.7 g (82 mmol) of potassium hydroxide was added while stirring at room temperature under a nitrogen atmosphere.Thereafter, the temperature was raised to 60 C. for 5 hours, and disappearance of 2- [chloro (4-chlorophenyl) methyl] pyridine was confirmed by TLC.After allowing to cool, dimethylsulfoxide was distilled off, methylene chloride and water were added, and then 1N hydrochloric acid was added to neutralize.After separating the aqueous layer, the organic layer was concentrated(37 mmol, yield 87%) of 4- [4 - [(4-chlorophenyl) (2-pyridyl) methoxy] piperidino] butanoic acid.To a solution of General procedure: To a stirred solution of (1-(2-phenoxyethyl)piperidin-4-yl)methanol (0.3 g, 1.27 mmol) in THF (5 mL) was added sodium hydride (0.046 g, 1.9 mmol, 1.5 equiv) and 10 minutes later, General procedure: To a stirred solution of N-((4-chlorophenyl)(pyridin-2-yl)methyl)piperidine-4-carboxamide(Int-I) (0.20 g, 0.60 mmol) in CH3CN (5 mL) were added potassium carbonate (0.25 1 g, 1.81mmol, 3 equiv) and 1-(2-bromoethoxy)-3-chlorobenzene (0.143 g, 0.60 mmol, 1 equiv) at room temperature. The reaction mixture was heated at 80 °C and stirred for 6 h. After completion, the reaction mixture was diluted with water and extracted with CH2C12. The combined organic extract was dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification using silica gel column chromatography (3percent MeOH/ CH2C12as eluent) afforded 0.05 g of 1-(2-(3-chlorophenoxy) ethyl)-N-((4-chlorophenyl) (pyridin-2-yl) methyl) piperidine-4-carboxamide (Yield = 17percent). Title compound was prepared from The compounds (I) (1.2 kg) and (II) (1.0 kg, X1'Cl,

Molecular Weight:238.11
XLogP3:3.4
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:237.0112047
Monoisotopic Mass:237.0112047
Topological Polar Surface Area:12.9
Heavy Atom Count:15
Complexity:190
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes