Hydrochloric Acid → HCID 20186859, compound

Participants

Reaction Steps

To a solution of 1-chloro-3-[4-(4-chlorobenzyl)piperazin-1-yl]propane (50 g, 0.174 mole, prepared as in EP No. 10392) in butanone (250 ml) was added sodium iodide (26.09 g, 0.174 mole) and the mixture was stirred for 45 minutes under N2. This solution was then added dropwise to a stirred, refluxing mixture of resorcinol (95.84 g, 0.87 mole), anhydrous potassium carbonate (24.06 g, 0.174 mole) and butanone (400 ml) which had previously been heated to reflux for 1.5 hours. After a further 26 hours at reflux the mixture was cooled and filtered. Concentration in vacuo afforded a brown oil which was redissolved in ethanol (500 ml) and acidified with ethanolic hydrogen chloride (400 ml). The resulting precipitate was filtered off under N2, washed with ethanol and dissolved in water (1.25 liters) at 50° C. Saturated aqueous sodium bicarbonate solution was added to pH 7 and the product extracted into dichloromethane. Evaporation of the dried extracts gave a white solid which on trituration with ether gave 45.82 g (73%) of the title compound of mp (EtOH) 134°-135° C., νmax (KBr) 1490, 1600, 2820, 2870, 2940, 3420 cm-1, δ(DMSO) 1.98 (2H, m, CH2CH2CH2), 2.56 (8H, bs, N--CH2 [piperazine]), 2.6 (2H, t, N--CH2), 3.48 (2H, s, CH2Ar), 3.92 (2H, t, J=6 Hz, O--CH2), 5.6 (1H, broad exchangeable, OH), 6.32-6.41 (3H, m, aromatic), 7.06 (1H, t, J=8 Hz, resorcinol C--5H), 7.25 (4H, d.d, J=13 Hz, 8.5 Hz, chlorobenzyl aromatic).

Provenance & Evidence