Water → HCID 18790020, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-adamantylamine (12.0 grams; 0.079 moles) in 250 cc of DMF is prepared. Triethylamine (21.9 cc; 0.158 moles), is added and the mixture is warmed to about 50° C. To the warm solution, there is added over a period of 3 hours, 1-(2-pyridyl)-4-(2-bromo-1-methylethyl)piperazine (18.0 grams; 0.063 moles) keeping the temperature about the same. The reaction mixture is poured into 500 cc of water and then extracted with ether. The ethereal phase, washed with water, then washed to neutrality and allowed to evaporate, gives as a residue, a crude oily product, which is purified by column chromatography. (THF-diisopropyl ether-Et3N 50:40:10). Compound (26) is an oil, which solidifies after prolonged standing; m.p. 67°-68° C. from n-hexane); Rf=0.22 (from ethyl acetate Et3N 9:1); IR (nujol) νmax: 1590, 1480, 1430, 1310, 1240, 1160, 775 cm-1 ; νN-H: 3250 cm-1 ; 1H-NMR (CDCl3): 0.93 (d, J=5 Hz; 3H); 1.20-2.23 (m; 16H); 2.23-3.00 (m; 7H); 3.20-3.70 (m; 4H); 6.40-6.73 (m; 2H; 7.23-7.63 (m; 1H); 8.03-8.27 (m; 1H); tripicrate: m.p. 185° C. (from ethanol).

Provenance & Evidence