Benzaldehyde → 1-[3-[4-(1,4-Benzodioxan-5-yl)-1-piperazinyl]-1-propyl]-3-benzyl-2-imidazolidinone, hydrochloride

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Reaction Steps

A solution of 1-[3-[4-(1,4-benzodioxan-5-yl)-1-piperazinyl]-1-propyl]-2-imidazolidinone (prepared from 1-(1,4-benzodioxan-5-yl)piperazin and 1-(3-chloro-1-propyl)-2-imidazolidinone by the method described in EXAMPLE 2) (2.5 g) and benzaldehyde (2.3 g) in glacial acetic acid (30 ml) was treated portionwise with sodium borohydride (0.6 g) keeping the temperature at 10° C. After stirring for 40 min. at room temperature additional benzaldehyde (2.3 g) and sodium borohydride (0.6 g) was added and the mixture stirred for 16 h at room temperature. Removal of solvent in vacuo gave a heavy oil which was applied to a silica gel column (eluent: ethyl acetate/ethanol/triethylamine=10:1:1). The title compound was isolated as a viscous oil which crystallized as the hydrochloride from an acetone/ether mixture by addition of an ether solution of dry HCl. Yield: 2.8 g, mp: 181°-91° C. 1H NMR (δ, DMSO): 1.90-2.10 (m, 2H), 3.00-3.25 (m, 10H), 3.30 (t, 2H), 3.35-3.65 (m, 4H) 4.20 (s, 4H), 4.25 (s, 2H), 6.50 (d, 1H), 6.55 (d, 1H), 6.75 (t, 1H), 7.00 (b, 2H), 7.20-7.40 (m, 5H).

Provenance & Evidence