Hydrochloric Acid → HCID 131724534, compound

Participants

Reaction Steps

To a solution of (±)-cis-2-phenyl-5,6,8,8a,9,10,11,11a-octahydro-4H-pyrido[3,2,1-ij]pyrrolo[3,4-c]quinoline, the free base of EXAMPLE 15, (20 mg, 0.07 mmol) in 2 mL of 1,2-dichloroethane was added 37% aqueous formaldehyde (0.010 mL, 0.11 mmol), sodium triacetoxyborohydride (37 mg, 0.17 mmol) and glacial acetic acid (1 drop). The resulting mixture was stirred at ambient temperature for 1 h and then the reaction was quenched with water. The mixture was partitioned between chloroform and saturated aqueous sodium carbonate. The organics were washed with brine, dried (K2CO3) and concentrated in vacuo. The residue was dissolved in 1 mL ethanol and 5 mL of ether and then there was added 2M HCl in ether (0.07 mL, 0.14 mmol). A solid precipitated out of solution. The solvents were decanted and the solid was triturated twice with ether and dried in vacuo to afford 20 mg (77%) of the title compound of EXAMPLE 16 as an off white powder. 1H NMR (d6-dmso): δ 7.55-7.50 (m, 2H), 71.35 (app t, 2H, J=7.5 Hz), 7.24-7.17 (m, 2H), 7.14 (s, 1H), 4.07-3.98 (m, 1H), 3.82-3.73 (m, 1H), 3.44-3.32 (m, 1H), 3.10-3.03 (m, 2H), 3.02-2.97 (m, 1H), 2.94-2.70 (m, 9H), 1.97-1.85 (m, 2H). LRMS (ES)+: 305.3 (M+H)+.

Provenance & Evidence