SYNTHESIS OF OCTYLAMINE

• A mixture of 1-bromooctane (19.3g, 0.1 mol), hexadecyltributylphosphonium bromide (5.1g, 0.01 mol), sodium azide (16.2g, 0.25 mol) and water (50 ml) is stirred at 80 °C for 8 hours. 

• The aqueous phase is carefully removed, the organic phase is diluted with toluene (15.5 ml), and then a solution of sodium borohydride (11.7g, 0.3 mol) in water (30 ml) is added in 30 minutes. 

• The mixture is stirred at 80 °C for 16 hours. 

• The layers are separated and the organic phase is extracted with 10 per cent hydrochloric acid. 

• The catalyst is recovered from the organic phase by removal of the solvent and is reused as isolated. Basification of the acid phase and extraction with ether affords octylamine, 11.4g (88%), b.p. 172-174 °C.