(1H-imidazol-2-ylmethyl)methylamine(SALTDATA: 2HCl) synthesis

Yield:473927-72-9 95%

Reaction Conditions:

with sodium borohydrid;methylamine in methanol;dichloromethane;

Steps:

37.F Part F.

Part F. Preparation of N-(1H-imidazol-2-ylmethyl)-N-methylamine To a flame-dried 500-mL flask was added methanol (200 mL), 2-imidazolecarboxaldehyde (5.0 g, 52 mmol), and 8.0 M methylamine (20 mL, 160 mmol). The reaction was stirred for 45 min, at which time, all carboxaldehyde dissolved. Sodium borohydride (4.0 g, 104 mmol) was added in four equal portions over a period of 2 min, resulting in a vigorous exotherm and a reaction temperature of 45° C. The reaction temperature was increased to 50° C. and maintained at this temperature for 2 h. The reaction was then cooled, concentrated, and dichloromethane (200 mL) was added. The mixture was concentrated, and dichloromethane (200 mL) was again added. The resulting mixture was filtered, the filter cake was washed with dichloromethane (2 50 mL), and the filtrate was concentrated. The resulting viscous yellow oil solidified upon standing to afford N-(1H-imidazol-2-ylmethyl)-N-methylamine as a yellow solid (5.5 g, 95%) which was used without further purification. ¹H-NMR (CDCl₃) δ 6.99 (s, 2H), 3.87 (s, 2H), 2.46 (s, 3H)

References:

US2003/212054,2003,A1