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

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).

1. waitthe mixture was left
2. additionwas added to salt out the organics
3. extractionThis mixture was extracted with CHCl3 (3×40 mL)
4. dry with materialdried over anhydrous K2CO3
5. filtrationThe solution was filtered
6. customthe solvent removed under vacuum
7. distillationThe crude (˜12 g) was distilled under reduced pressure (bp=63° C. at 0.1 mbar)

ORD record

ord-be1a58a6c6ca458fac1d1a2336e69711

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598217B2