Propyl chloroformate → HCID 86669257, compound

Participants

Reaction Steps

(cis)-1-Acetyl-2-ethyl-6-[4-(1-piperidinylmethyl)phenyl]-1,2,3,4-tetrahydro-4-quinolinamine (for a preparation see Intermediate 5) (50 mg, 0.128 mmol) was dissolved in dichloromethane (DCM) (2 mL), mixed with DIPEA (0.045 mL, 0.255 mmol) and propylchloroformate (0.019 mL, 0.166 mmol, Aldrich) and stirred under nitrogen. After 40 minutes the reaction was loaded onto a 5 g SCX-column, eluting with MeOH (70 mL) followed by 2M MeOH/NH3 (70 mL). Product-containing fractions were evaporated to dryness to give a colourless solid (38 mg). This was purified on a 12+M Biotage silica column, eluting with 0 to 8% 2M methanolic ammonia in DCM. Product-containing fractions were evaporated to dryness to give a clear, colourless solid (16 mg). LCMS (Method C): Rt=0.83, MH+=478

Provenance & Evidence