3-Phenoxybenzamide → 3-Phenoxy-benzylamine

Participants

Reaction Conditions

Reaction Steps

A solution of the product from step (a) (6.5 g) in THF (75 ml) was added under N2 over 15 minutes to a stirred suspension of LAH (2.3 g) in THF (100 ml). After addition was complete, the mixture was refluxed for 5.5 hours, then cooled to -5° C., excess LAH destroyed by the careful addition of 15% w/v aqu. NaOH (100 ml), and the mixture taken up in water (150 ml) and ether (200 ml). The aqueous phase was separated, extracted with ether and the combined ether solutions washed with 2N aqu. NaOH (2×100 ml) and water (2×200 ml), dried over Na2SO4 and evaporated in vacuo to give the desired product as a colourless oil (5.9 g). The 200 MHz 1H NMR was consistent with the proposed structure.

Provenance & Evidence