5-(1,2,4-triazolylmethyl)-N,N-dimethyltryptamine
A solution of formaldehyde (0.30 g of a 37%, w/v, solution, 3.7 mmol) in MeOH (10 mL) was added to a stirred mixture of 5-(1,2,4-triazolylmethyl)- tryptamine (0.36 g, 1.5 mmol), NaCNBH3 (0.225 g, 3.6 mmol), and glacial acetic acid (0.45 g, 7.5 mmol), in MeOH (10 mL), at 0°C. The solution was warmed to 25°C and stirred for 2 h before adding saturated K2CO3 solution (5 mL). The MeOH was removed under vacuum, H2O (10 mL) was added, and the mixture was extracted 3x with ethyl acetate. The combined extracts were washed once with brine and dried and the solvent evaporated. The crude product was chromatographed on silica gel eluting with CH2Cl2/EtOH/NH3 (40:8:1) to give 5-(1,2,4-triazolylmethyl)- N,N-dimethyltryptamine (0.21 g, 52%).
Reference: J. Med. Chem. 38, 1799-1810 (1995)