Hydrochloric Acid → HCID 19380977, compound

Participants

Reaction Steps

To an ice cooled solution of 1-(9,10-dihydro-9,10-methanoanthracen-9-ylcarbonyl)-4-(4-morpholinyl)piperidine (2.29 g, 5.89 mmol) in tetrahydrofuran (35 mL) was added 1M borane-tetrahydrofuran in tetrahydrofuran (17,7 mL, 17.7 mmol). The reaction was refluxed for 5 h and then was cooled with an ice bath. This mixture was added dropwise a solution of methanolic hydrochloride (25 mL). The ice bath was removed and the solution was refluxed for 0.5 h. The resulting precipitate was filtered with hexane wash (50 mL). The solid was recrystallized from acetonitrile to give the title compound as a white solid (1.62 g, 68%), mp 257.0°-259.0° C.; MS(CI): 375 (M+H); NMR (250 MHz,DMSO-d6): 2.27(m, 6H), 2.75(s, 2H), 3.11(br s, 2H), 3.40(br s, 2H), 3.66(m, 2H), 3.94(m, 4H), 4.38(m, 3H), 4.47(s, 1 H), 7.00(m, 4H), 7.34(m, 4H), 10.46(br s, 1H), 11.91(br s, 1H).

Provenance & Evidence