Hydroxyamine hydrochloride → HCID 76568486, compound

Participants

Reaction Steps

To a solution of 1′-benzylspiro[indene-1,4′-piperidin]-3(2H)-one lab (38 g, 0.15 mol) in EtOH (300 mL), hydroxylamine hydrochloride (18 g, 0.30 mol) and sodium acetate (19.5 g, 0.275 mol) were added. The mixture was refluxed for 4 hours and the solvent removed under reduced pressure. The residue was diluted with 150 mL water and 100 mL CH2Cl2. After the mixture was stirred for 10 min, the resulting white solid was collected by filtration. The organic phase in the filtrate was separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with brine and dried over Na2SO4. After evaporation of the solvent under reduced pressure, a yellow oil was obtained. The oil was crystallized from EtOAc to yield 1′-benzylspiro[indene-1,4′-piperidin]-3(2H)-one oxime 1ac as an off-white solid. 1H NMR (CD3OD, 400 MHz) δ 7.64 (d, J=8.0 Hz, 1H), 7.55-7.57 (m, 2H), 7.38-7.50 (m, 5H), 7.29-7.33 (m, 1H), 4.25 (s, 2H), 3.41 (d, J=12.4 Hz, 2H), 3.08 (t, J=12.0 Hz, 2H), 2.95 (s, 2H), 2.20-2.28 (m, 2H), 1.68 (d, J=14.4 Hz, 2H).

Provenance & Evidence