Phenethylamine → Benzyl-[8-(4-benzyl-piperazin-1-yl)-quinolin-6-yl]-methyamine

Participants

Reaction Conditions

Reaction Steps

To an oven-dried 25 mL round bottom flask was added Cs2CO3 (1.55 g, 4.76 mmol), BINAP (300 mg, 3 mol %), Pd(OAc)2 (100 mg, 3 mol %) and kept under vacuum overnight. To this reaction vessel under a nitrogen atmosphere was added 8-(4-benzyl-piperazin-1-yl)-6-bromo-quinoline (1.3 g, 3.4 mmol), anhydrous toluene (12 mL) and benzylmethylamine (0.53 mL, 4.1 mmol). The reaction mixture was heated at 100° C. overnight. The cooled reaction mixture was diluted with Et2O (15 mL), filtered to remove solids, washed with EtOAc (10 mL) and concentrated. The resulting oil was purified by column chromatography (40% EtOAc/hexane) affording 830 mg (59%) of benzyl-[8-(4-benzyl-piperazin-1-yl)-quinolin-6-yl]-methyamine as an orange foam.

Provenance & Evidence