Potassium Iodide → HCID 22824882, compound

Participants

Reaction Conditions

Reaction Steps

In 50 ml dry dimethylformamide (DMF) were combined 5.00 g (22.2 mmol) 2,3-dihydro-spiro[benzofuran-2(3H),3'-piperidine]hydrochloride of Example 1c, 7.41 g (1.25 equivalents) 3-(3-chloropropyl)-6-fluoro-1,2-benzisoxazole of Example 1d, 18.4 g (6 equivalents) milled anhydrous potassium carbonate, and a catalytic amount (0.5 g) potassium iodide. The mixture was stirred under nitrogen at 90° C. for three and one-half hours, then cooled and filtered. The DMF was evaporated in vacuo to an oil which was partitioned between 10% K2CO3 and ether. The ether was separated, washed with water, saturated aqueous alt solution, dried over MgSO4, filtered, and passed through a column of 40 g alumina in ether. The product-containing fractions were combined and adjusted to pH 1 with ethereal-HCl. The resultant precipitate was collected and recrystallized from 1:1 dichloromethane/ethyl acetate to yield 3.36 g (38%) of (R,S)-dihydro-1'-[3-(6-fluoro-1,2-benzisoxazol-3-yl)propyl]-spiro[benzofuran-2(3H),3'-piperidine]hydrochloride, m.p. 257°-259° C.

Provenance & Evidence