Triethylamine → HCID 21073733, compound

Participants

Reaction Steps

To a suspension of 1-(6-methyl-pyridin-2-yl)-piperazine bishydrochloride (0.77 g, 3.08 mmol) in dichloroethane (10 mL) was added Et3N (1.0 mL, 7.17 mmol) and the mixture was stirred for 30 min. 4-(7-Oxo-5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yloxy)-butyraldehyde (0.85 g, 3.63 mmol) was added as a solution in dichloroethane (3 mL) and the mixture was stirred at room temperature for 15 min. NaBH(OAc)3 (1.1 g, 5.2 mmol) was added as a solid and the mixture was stirred at room temperature for 3 h. The reaction was poured into EtOAc and washed with saturated NaHCO3 and brine, dried over MgSO4 and concentrated. The residue was partitioned between EtOAc and pH 4.5 aqueous citric acid. The product went into the aqueous layer selectively over the impurities. The aqueous layer was neutralized with solid NaHCO3 to pH 8 and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4 and concentrated to give the title compound as a sticky foam (0.77 g). The foam was dissolved in Et2O and treated with anhydrous HCl gas to give a white precipitate. The mixture was filtered, washed with Et2O and hexanes, and dried to give a white solid (616 mg). MS: APCI: M+1: 396.1 (Exact Mass: 395.23).

Provenance & Evidence