Hydrochloric Acid → 1-(1H-Imidazol-1-yl)-N,N-dimethylmethanamine

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Reaction Steps

Imidazole (5 g, 73.5 mmol) and dimethylamine hydrochloride (6 g, 73.5 mmol) were stirred in water (12.5 mL) at room temperature. The solution was gradually acidified to pH 5 by the addition of conc. aqueous HCl. A solution of formaldehyde (37% in water; 6.05 mL, 80.8 mmol) was added and the mixture was left to stand for 16 hours. Then it was basified with an excess of 20% KOH solution (˜40 mL) and K2CO3 (˜6 g) was added to salt out the organics. This mixture was extracted with CHCl3 (3×40 mL) and dried over anhydrous K2CO3. The solution was filtered and the solvent removed under vacuum. The crude (˜12 g) was distilled under reduced pressure (bp=63° C. at 0.1 mbar) to yield Imidazol-1-ylmethyl-dimethyl-amine as a colourless oil (6.1 g, 66%). 1H NMR (400 MHz, CDCl3): 7.51 (1H, s), 7.02 (2H, bs), 4.67 (2H, s), 2.29 (6H, s).

Provenance & Evidence