Triphenylphosphine → Ammonia

Participants

Reaction Steps

A mixture of 3-chloro-5-hydroxy-N,N-diisopropyl-benzamide (0.05 g), 2-(pyridin-4-yl-amino)-butan-1-ol (0.023 g), triphenylphosphine (0.04 g) and toluene (1 ml), was treated with diisopropyl azodicarboxylate (0.03 ml) and the resultant solution stirred under nitrogen for 8 days. The reaction mixture was concentrated under reduced pressure and the residue purified by flash column chromatography, eluting with chloroform:methanol:aqueous ammonia (90:10:1) to give an impure sample of the title compound. This impure sample was subjected to preparative H.p.l.c. (system A) and the purified material was treated with 1M hydrogen chloride in diethyl ether to give the title compound as a gum (0.002 g).

Provenance & Evidence