Hydrochloric Acid → HCID 45275783, compound

Participants

Reaction Steps

To a solution of 1-(3,5-dichloropyridin-4-yl)piperidine-4-carboxamide 23 (30 mg, 0.11 mmol) in THF (2 mL), at 0° C., was added a 1M solution of borane THF complex in THF (11.1 mL, 1.1 mmol). The reaction was stirred for 1 hour before warming to r.t. and stirring for a further 18 hr. To the reaction was added 2M HCl (2 ml), the mixture diluted with water (20 ml) and extracted with EtOAc (2×20 mL) and the combined organic extracts were washed with brine (25 mL). The combined aqueous extracts were basified with saturated sodium hydrogen carbonate and then extracted with EtOAc (2×20 mL). The combined organic extracts were washed with brine (20 mL), dried (MgSO4) and concentrated under reduced pressure to give a crude colourless oil (8 mg). The crude product was purified by flash column chromatography on silica gel (CH2Cl2, MeOH, 97:3 to CH2Cl2, 1 M methanolic NH3, 9:1) to furnish the title compound, LC-MS (ESI, 3.5 min) Rt 1.45 min, m/z 260 (91%, [M+H]+).

Provenance & Evidence