Acetic Acid → HCID 57494025, compound

Participants

Reaction Steps

To a mixture of 4-(2-methoxy-ethylamino)-piperidine-1-carboxylic acid tert-butyl ester (465 mg), and 2-thiazolecarboxaldehyde (190 μl) stirring in anhydrous 1,2-dichloroethane (5 ml) was added glacial acetic acid (1 equiv.) and sodium triacetoxyborohydride (458 mg). The reaction mixture was stirred for 12 hours at room temperature, then diluted with dichloromethane (40 ml), washed with brine, dried (MgSO4) and the solvents removed in vacuo. The residue was purified using flash silica chromatography to give 4[(2-methoxy-ethyl)-thiazol-2-ylmethyl-amino]-piperidine-1-carboxylic acid tert-butyl ester (574 mg). Treatment of this compound with HCl in dichloromethane/methanol and a basic wash with sodium hydrogen carbonate yielded (2-methoxy-ethyl)-piperidin-4-yl-thiazol-2-ylmethyl-amine.

Provenance & Evidence