Formaldehyde → HCID 59752627, compound

Participants

Reaction Steps

To a solution of 33.5 mg of 2,3-diphenyl-2,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene (Example 176, Step D) in 5 mL of CH2Cl2 were added 0.15 g of paraformaldehyde and 0.15 g of NaBH(OAc)3. The mixture was stirred at RT for 12 h and was diluted with 20 mL of 1 M NaOH. After stirring for 3 h, the mixture was extracted with CH2Cl2 (2×10 mL) and the combined organic layers were concentrated. Chromatography on SiO2 (0 to 5% 2 M NH3 in MeOH/CH2Cl2) gave 22.3 mg of the title compound as a white solid. MS (ESI): exact mass calculated for C20H21N3, 303.17; found, m/z 304.2 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.35-7.30 (m, 3H), 7.27-7.21 (m, 2H), 7.20-7.16 (m, 3H), 7.15-7.12 (m, 2H), 3.06-3.02 (m, 2H), 2.83-2.79 (m, 2H), 2.72-2.67 (m, 4H), 2.50 (s, 3H).

Provenance & Evidence