Triethylamine → HCID 66906019, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-chloronicotinate (890 mg, 1.00 equiv; 5.03 mmol) in dry DMF (30 mL) is added 4-hydroxypiperidine (1.5 equiv; 7.55 mmol; 778.95 mg) and triethylamine (1.05 mL; 1.5 equiv; 7.55 mmol). The system is flushed with N2 and heated at 80° C. for 4.5 h. The reaction is allowed to reach room temperature and is diluted with water/EtOAc. The aqueous layer is extracted with ethyl acetate (3×). The organic layer is washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude residue is purified via chromatography eluting with hexane/EtOAc 2:1 to 1:2 to yield an orange solid. The solid is triturated with hexane/EtOAc 4:1 and filtered to provide the title compound (1.023 g, 86%) as a white solid. ES/MS m/z 237.0 (M+1)

Provenance & Evidence