Formaldehyde → cis-[5-(1-Methyl-piperidin-4-yl)-thiophen-3-yl]-(octahydro-quinolin-1-yl)-methanone

Participants

Reaction Conditions

Reaction Steps

cis-(Octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone (CC-033) (0.070 g, 0.21 mmol) was dissolved in aqueous formaldehyde (37% w/w; 0.1 mL) and formic acid (1 mL). The reaction was heated to 150° C. using microwave irradiation for 5 minutes. The product was purified by flash chromatography on a SCX-2 cartridge, eluting with acetonitrile and then 2 M ammonia in methanol. The residue was further purified by flash chromatography on a NH2-SPE cartridge, eluting with 0%-100% ethyl acetate in cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound (0.035 g). LCMS m/z 347.21 min [M+H]+ RT=6.68 min (Analytical Method 1). 1H NMR (400 MHz, CHCl3-d): δ 7.2 (s, 1H), 6.85 (s, 1H), 4.7 (m, 1H), 3.8 (m, 1H), 3.1 (m, 1H), 2.9 (m, 1H), 2.8-2.7 (m, 1H), 2.30 (s, 3H), 2.1-1.1 (m, 20H).

Provenance & Evidence