Dimethylformamide → HCID 131722786, compound

Participants

Reaction Steps

A mixture of the product of Example 7, Step (b) (271 mg, 0.89 mmole), methyl benzylamine (2.42 mg, 2.00 inmoles), tetra-n-butylammonium iodide (37 mg, 10 mmole %), and anhydrous potassium carbonate (2.76 mg, 2.00 mmoles) in 1.0 mL DMF was stirred overnight at 80-86°. After cooling, the mixture was partitioned between diethyl ether and water. The aqueous layer was extracted with ether, the combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and the solvent evaporated. Chromatography of the residue over silica gel using 20% ethyl acetate-hexane as eluent gave the title compound as the free base. A methanol solution of the free base was acidified with a solution of hydrochloric chloride in methanol, the solvent evaporated, and the residue crystallized from ethyl acetate-hexane to give a product compound (53 mg) as a white crystalline solid, characterized as follows: Analysis for C23H28ClF3N2•¼ H2O (mw 429.44): Calculated: C, 64.35; H, 6.69; N, 6.52; Found: C, 64.60; H, 6.70; N, 6.52.

Provenance & Evidence