Acetic Acid → HCID 59543456, compound

Participants

Reaction Steps

5-Bromo-1′,2′,3′,4′,5′,6′-hexahydro-[2,4′]bipyridinyl (6.4 g, 18.02 mmol) was dissolved in 2% acetic acid in MeOH (40 ml). Propanone (8 mL, 113 mmol) and Na(CN)BH3 (3.6 g, 57 mmol) were added. The reaction mixture was stirred at RT overnight. The reaction mixture was added 1N HCl, filtered and concentrated in vacuo. The compound was dissolved in water and the pH was adjusted to 12, then extracted with DCM (3×200 mL). The crude product was treated with 1N HCl for 1 hour and extracted with diethyl ether to remove impurities. The aqueous phase was pH adjusted to pH=5.8-9. Extraction with ethyl acetate (3×100 mL) The organic phase was dried with Na2CO3, filtered and evaporation gave 4.6 g (86%) white crystals.

Provenance & Evidence