Trifluoroacetic acid → HCID 70207845, compound

Participants

Reaction Steps

To a 2 g sample of the compound from step 7b above in 10 mL of CH2Cl2 at 0° C. was added 10 mL of TFA, and the reaction mixture was stirred for 1 hour, poured into saturated aqueous Na2CO3 and extracted with CH2Cl2. The organic extract was dried over MgSO4, and the solvent was removed. The residue was chromatographed on silica gel, eluting with 99:1 to 95:5 CHCl3 :MeOH. The product was treated with HCl/ether, and the salt was recrystallized from EtOH/EtOAc to give 1.2 g of title compound: 1H NMR (D2O, 300 MHz) δ 2.18-2.50 (m, 3H), 2.54-2.65 (m, 1H), 3.51-3.36 (m, 2H), 5.06 (t, 1H, J=8 Hz), 7.26 (d, 1H, J=0.7 Hz), 8.24 (dd, 1H, J=0.7, 1.8 Hz), 8.60 (d, 1H, J=1.8 Hz); MS m/z: 223 (M+H)+, 240 (M+NH4)+ ; Anal. Calcd for C11H11N2OCl.2.0 HCl: C, 44.69; H, 4.43; N, 9.47. Found: C, 44.57; H, 4.31; N, 9.33.

Provenance & Evidence