Hydrochloric Acid → 2-(2-Aminophenyl)-N-methyl-N-[(1S)-1-(3-aminophenyl)-2-(1-pyrrolidinyl)ethyl]acetamide

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Reaction Conditions

Reaction Steps

With stirring at 55° C., Raney nickel was added in small quantities to a mixture of 10 (0.9857 g, 2.3899 mmol) and hydrazine hydrate (55%, 2 mL) in EtOH (30 mL) until gas evolution stopped in about 10 min. The mixture was then filtered through celite, and the Raney nickel was washed with hot MeOH (100 mL). The filtrate was evaporated and dried in vacuo before the residue was partitioned between sat'd NaHCO3 and CH2Cl2, which was dried (Na2SO4), filtered through celite, and evaporated. The product was gravity column chromatographed eluting with CHCl3:2% NH3:2% MeOH before it was converted to the HCl salt with Et2O—HCl to yield 9 3HCl.(0.3159 g, 29%, unoptimized): m.p. (HCl salt) 219-222° C.; 1H NMR (HCl salt, DMSO-d6) δ1.98 (br s, 4H, —CH2CH2—), 2.87 (s, 3H, —NCH3), 3.2-4.3 (complex, 8H, 4 —CH2—), 6.1 (m, 1H, —CH—), 7.11-7.45 (complex, 8H, aromatic). MS(FAB) m/z 353. Anal. (C, H, N) C21H28N4O. 3HCl0.25H2O.

Provenance & Evidence