Hexahydro-1,4-diazepine → 7-Cyclopropyl-8-(1,4-diazepan-1-yl)quinoline

Participants

Reaction Conditions

Reaction Steps

A mixture of homopiperazine (0.965 g, 9.6 mmol), NaOt-Bu (0.323 g, 3.4 mmol), (±)-BINAP (0.40 g, 0.64 mmol), and Pd2(dba)3 (0.22 g, 0.24 mmol) in toluene (10 mL) was heated to 110° C. and 8-bromo-7-cyclopropylquinoline (0.60 g, 2.4 mmol) was added. After 2 h, the reaction was cooled to rt, quenched with 50 mL of water, and extracted with EtOAc (2×50 mL). The organic layer was separated, dried over anhydrous Na2SO4, concentrated, and purified by SiO2 chromatography with a gradient elution of 0.25-2.2% NH4OH and 2.5-22% MeOH/CH2Cl2 to yield 7-cyclopropyl-8-(1,4-diazepan-1-yl)quinoline (0.33 g, 51% yield).

Provenance & Evidence