Formaldehyde → HCID 10331376, compound

Participants

Reaction Steps

A flask containing Cis 2-(1,2,3,3a,9,9a-Hexahydro-cyclopenta[b]quinolin-4-yl)-ethylamine (0.18 g, 0.84 mmol) and 0.07 ml of 37% aqueous formaldehyde in 2 ml of EtOH was treated with TFA (0.07 mL, 0.92 mmol) at room temperature for 1 hr. The mixture was concentrated under reduced pressure, and the residue was taken up in dichloromethane, washed with 1 N NaOH (15 mL), Brine (15 mL) and then dried with MgSO4. Evaporation and flash chromatography (10% 2N NH3 in ethanol/dichloromethane) afforded the title compound, which was converted to the HCl salt to give a brown solid (0.19 mg, 85%): The same step 5 procedure was used to prepare the trans isomer except that Trans 2-(1,2,3,3a,9,9a-Hexahydro-cyclopenta[b]quinolin-4-yl)-ethylamine was used instead of the cis isomer.

Provenance & Evidence