Pyrrolidine → HCID 22641327, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3.1 g of (10.9 mmol) of 7-benzyloxy-4-chloro-6-fluoro-2-methyl-quinoline and 18.1 ml (21.8 mmol) pyrrolidine was heated at 80° C. (oil bath temperature) under an argon atmosphere for 6 h. The reaction mixture was concentrated in vacuo, the residue taken up in methylene chloride, which was washed with water, saturated NaCl solution and then dried over magnesium sulphate. The solvent was removed in vacuo, the residue purified by flash chromatography on silica gel with CH2Cl2/MeOH (100:0 to 90:10 over 1 h) as eluent. Combination of the purified fractions and concentration in vacuo gave 1.7 g (46.2%) of the 7-benzyloxy-6-fluoro-2-methyl-4-pyrrolidin-1-yl-quinoline as a brown crystalline solid. ISP mass spectrum, m/e: 337.4 (M+1 calculated for C21H21FN2O: 337).

Provenance & Evidence