Formaldehyde → HCID 68936514, compound

Participants

Reaction Steps

To a mixture of 4-methyl-1-(3-piperidin-4-yl-propyl)-2,3-dihydro-1H-indole (1.50 g, 5.81 mmol) in dichloroethane (20 mL) was added formaldehyde (37% in water; 4.0 mL) and Na(OAc)3BH (6.39 g, 30.1 mmol). After 1 h, the mixture was quenched with satd. aq. NaHCO3 and extracted with CHCl3. The organic layer was dried (Na2SO4) and concentrated to obtain the crude residue, which was purified by FCC to give 1.03 g (66%). MS: mass calcd. for C18H28FN5, 272.23; m/z found, 273.4 [M+H]+. 1H NMR (CDCl3): 6.97 (t, J=7.7, 1H), 6.47 (d, J=7.6, 1H), 6.29 (d, J=7.8, 1H), 3.33 (t, J=8.4, 2H), 3.01 (m, 2H), 2.91-2.81 (m, 4H), 2.26 (s, 3H), 2.19 (s, 3H), 1.95-1.86 (m, 2H), 1.74-1.53 (m, 4H), 1.37-1.16 (m, 5H).

Provenance & Evidence