1,3-Propanediamine → HCID 178444777, compound

Participants

Reaction Conditions

Reaction Steps

3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane (1.00 g, 4.06 mmol, Example 1) was added in portions over a period of 20 minutes to a stirred solution of 1,3-diaminopropane (1.0 g, 13.50 mmol) in dry acetonitrile at 50° C. After the addition, the reaction mixture was maintained at 50° C. for an additional 30 minutes. The reaction mixture was then cooled and filtered to provide the title compound as a yellow colored solid. For further purification, the solid was suspended in a small amount of water, stirred and filtered to afford the title product in >97% purity; yield: 0.78 g, (68%); mp. 136°-137° C. 1H NMR (DMSO-d6) δ 1.19 [s, 6H, C(CH3)3 ], 1.37 (m, CH2CH2CH2), 1.52 (bs, 1N, NH), 2.21 & 1.54 (2t, 4H, NHCH2), 5.22 (s, 2H, imida-CH2), 7.05 & 7.27 (2s, 2H, imida-ring H) and 11.42 (bs, 1H, NOH). MS m/e 285 (M+H)+.

Provenance & Evidence