Hydrochloric Acid → HCID 69487499, compound

Participants

Reaction Steps

To a solution of [4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethyl}-amine 2 (0.03 g, 0.06 mmol) in acetonitrile (2 ml) formaldehyde (36%, 0.1 ml) and sodium cyanoborohydride (0.012 g, 0.019 mmol) are added. After stirring at room temperature for 10 min the pH is set to 2 by adding conc. hydrochloric acid and stirring is continued for 2 h. The solvents are evaporated, the crude product suspended in water (10 ml) and the pH adjusted to 9 with aqueous ammonia. The mixture is extracted with ethyl acetate (3×25 ml), the organic phase washed with brine and dried over sodium sulfate. After concentration in vacuo the oily residue is precipitated with heptanes to yield methyl-[4-(4-[1,2,3]triazol-1-yl-butyl)-phenyl]-{2-[2-(4-trifluoromethyl-phenyl)-vinyl]-oxazol-4-ylmethyl}-amine 3 as a light yellow solid. Yield 31 mg (100%); m.p. 112–114° C.

Provenance & Evidence