Potassium Carbonate → HCID 22641500, compound

Participants

Reaction Steps

A mixture of 114 mg (0.5 mmol) of 2-methyl-4-pyrrolidin-1-yl-quinolin-7-ol, product of example 2, 166 mg (0.6 mmol) of potassium carbonate and 84 μl (0.6 mmol) of 3-methoxybenzyl chloride was heated at 80° C. in 8 ml of DMF under an argon atmosphere for 23 h. The mixture was cooled to RT and partitioned between EtOAc and water. The organic layer was separated, washed with water then saturated NaCl solution, dried over magnesium sulphate and concentrated in vacuo. The residue was taken up in diethyl ether and some not dissolved material was removed by filtration. The filtrate was treated under stirring with 0.25 ml of 3N HCL in MeOH and stirring was continued for 1 h. The solid that precipitated was filtered off by suction and dried in a high vacuum to give 138 mg (69.7%) of 7-(3-methoxy-benzyloxy)-2-methyl-4-pyrrolidin-1-yl-quinoline hydrochloride as an light-yellow solid. ISP mass spectrum, m/e: 349.4 (M+1 calculated for C22H24N2O2: 349).

Provenance & Evidence