Triethylamine → HCID 18615538, compound

Participants

Reaction Steps

At 0° C., 3.26 g (16 mmol) of 2,6-bischloromethyl4-methylphenol are added in portions to a solution of 5 g (32 mmol) of 1,4-dimethyl-1,4,7-triazacyclononane and 3.21 g (32 mmol) of triethylamine in 150 ml of methanol, and the mixture is stirred for 4 days at room temperature. For work-up, 1.28 g (32 mmol) of sodium hydroxide are added, and the sodium chloride which forms is filtered off. The solvent is removed under reduced pressure and the product is dried for one day under a high vacuum. Yield: 6.1 g (86%). Analysis: 1H-NMR:δ=2.24 (s,3 H, Carom.—CH3); 2.35 (s,12 H, N-CH3); 2.64 (m, 8 H, Carom.—CH2—N—CH2—CH2—N); 2.67 (s, 8 H, H3C—N—CH2—CH2—N—CH3); 2.87 (m, 8 H, Carom.—CH2N—CH2—CH2—N); 3.73 (s, 4 H, Carom.—CH2N); 6.82 (s, 2 H, Carom—H) 13C-NMR: 6=20.4 (Carom.—CH3); 45.4 (N—CH3); 53.0; 55.9; 56.2; (N—CH2—CH2—N); 58.6 (Carom.—CH2—N); 123.0 (Carom.—CH2—N); 127.4 (Carom.—CH3); 130.0 (Carom.—H), 154.7 (Carom.—OH) MS: (electrospray) m/e=447 (M+H⊕, 100%)

Provenance & Evidence