Dichloromethane → HCID 70204345, compound

Participants

Reaction Conditions

Reaction Steps

To a 700 mg sample of the compound from step 9c above in 5 mL of CH2Cl2 at 0° C. was added 5 mL of TFA. The reaction mixture was stirred for 1 hour at 0° C. then poured into saturated Na2CO3, and the layers were separated. The aqueous layer was extracted with CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated, and the residue was chromatographed on silica gel, eluting with 100:0 to 95:5 CHCl3 :MeOH. The product was converted to the salt by treatment with HCl/ether, which was recrystallized from ethanol/EtOAc: 1H NMR (D2O, 300 MHz) δ 2.19-2.52 (m, 3H), 2.64 (m, 1H), 3.53-3.58 (m, 2H), 5.13 (t, 1H, J=8 Hz), 7.34 (s, 1H), 8.05 (dd, 1H, J=0.8, 5.8 Hz), 8.49 (d, 1H, J=5.8 Hz), 9.07 (s, 1H); MS m/z: 189 (M+H)+, 206 (M+NH4)+ ; Anal. Calcd for C11H12N2O·2.0 HCl.H2O: C, 47.33; H, 5.78; N, 10.03. Found: C, 47.32; H, 5.83; N, 9.90.

Provenance & Evidence