128396-57-6 → HCID 15068036, compound

Participants

Reaction Steps

A mixture of 8-[4-[4-(1,2-benzisothiazol-3 yl)-1piperazinyl]butyl]-6-hydroxy-8-azaspiro[4.5]decane-7,9dione (1.14 g, 2.5 mmol) and KF-Al2O3 (0.36 g, ~1 equiv) in acetonitrile (25 mL) was vigorously stirred at room temperature under Ar for 4 h. The supernatant was then decanted and replaced with fresh acetonitrile (25 mL), and stirring was continued for 4 h. This process was repeated until the residue contained no more starting material (5× in total). The combined supernatants were evaporated and the resulting gum was purified by flash chromatography (EtOAc, then EtOAc acetone (1:1) to give the title compound (0.75 g, 66%) as an off-white foam. A 650 mg sample of the title compound was dissolved in excess ethanolic HCl and the solution was evaporated to dryness. The residue was taken up in acetone, ether was added and the resulting solid was collected and dried in vacuo to give 620 mg of a cream-colored powder, m.p. 194-197° C. An analytical sample was prepared by trituration with acetone to give the hydrochloride as a white powder; IR (CH2Cl2) 3430, 1785, 1680 cm-1 ; 1H NMR (CDCl3) δ 7.86-7.80 (m, 2H), 7.54-7.36 (m, 2H), 7.29 (b s, 1H), 4.77 (s, 1H), 4.12-4.08 (m, 4H), 3.56-3.50 (m, 2H), 3.47-3.33 (m, 2H), 3.14-3.04 (m, 4H), 2.62, 2.37 (q, J=17.1 Hz, 2H), 2.1-1.4 (b m, 13H); Anal. calcd for C24H32N4O3S/1.4 HCl:

Provenance & Evidence