Methane → HCID 22218623, compound

Participants

Reaction Steps

A solution of 350 mL of methanesulfonic acid in 1345 mL of ethyl acetate was added to a solution of 285.8 g of N,N′-bis(3-aminopropyl)cyclohexane-1,4-diamine (I) in 6880 mL of methanol. After stirring for 2 h, filtering, washing with ethanol and drying, 625 g of a crude solid were obtained. The solid was treated and stirred with water (5 mL per gram of solid) and activated charcoal for 2 h. After filtering off the charcoal, evaporating the water under vacuum, and drying at 40° C. until constant weight, 515 g (67.2%) of the title compound were obtained, with a melting point of 261-5° C. 1H-NMR spectrum (δ, ppm, DMSO-d6): 1.4 (m, 4H), 1.91 (m, 4H), 2.14 (m, 4H), 2.3 (s, 12H), 2.90 and 3.20 (m 10H), 8 (10 H). 13C-NMR spectrum (δ, ppm, DMSO-d6): 22.4 (cyclohexane CH2), 24.6 (CH2), 34.6 (CH2—NH2), 38.5 (acid CH3), 38.6 (acid CH3), 39.6 (CH2—NH), 52.9 (cyclohexane CH). IR spectrum (cm−1, KBr): 3440 (H2O), 2944, 2860 (aliphatic CH), 1195 (SO3). Elemental analysis (%): theory, C 30.48, H 7.30, N 8.88; found, C 30.79, H 7.04, N 8.88.

Provenance & Evidence