Ammonia → HCID 23447961, compound

Participants

Reaction Conditions

Reaction Steps

Compound 78 (0.11 g, 0.28 mmol) was dissolved in dry methylene chloride/THF, 1:1 (5 mL) and cooled to −20° C. Triethylamine (78 μL, 0.56 mmol) was added and then i-butyl chloroformate (37 μL, 028 mmol). After 10 min, ammonia in methylene chloride (0.5 mL, 1.1M, 0.56 mmol) was added and the temperature was allowed to rise slowly to 25° C. After 3 h, the solvent was removed in vacuo and the residue was purified by chromatograpy on silica (CH2Cl2/MeOH/NH3, 95:5:1 and 90:10:1) to give 70 mg (62%). Treatment with HCl in methanol 3 h at 50° C., removal of solvent in vacuo and chromatograpy on silica (CH2Cl2MeOH/NH3, 90:10:1 and 80:20:1) gave the free amine which was converted to the dihydrochloride salt 82. Mp: 192-200° C. IR (KBr) (cm−1): 3939(br), 3184(br), 2700(br), 1665, 1610, 1565, 1426. MS (amine): 295, 250, 210, 165, 152. 1H NMR: (amine, CD3OD): δ=7.96-7.22 (m, 9H, Ar—H), 4.93 (s, 2H, NH), 4.40 (s, 1H, Ar2CH), 2.94+2.46 (2m, 8H, piperazine-H). Anal. calc. for C18H21N3O×2HCl×1.1H2O, C, 55.70; H,6.54; N, 10.83. Found C, 55.83; H, 6.76; N, 10.75.

Provenance & Evidence