14-aminotetradecan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of N-(14-hydroxytetradecyl)phthalimide in 100 ml of methanol was added 0.87 g of hydrazine monohydrate and the mixture was heated under reflux for 3 hours. The reaction solution was distilled under reduced pressure and the residue was diluted with a 1N aqueous solution of sodium hydroxide and then extracted twice with chloroform. The organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and then distilled under reduced pressure. Chromatography over silica gel afforded the title compound as a colorless crystal. the mixture was heated under reflux for 3 hours The reaction solution was distilled under reduced pressure the residue was diluted with a 1N aqueous solution of sodium hydroxide extracted twice with chloroform washed with a saturated aqueous solution of sodium chloride dried over anhydrous sodium sulfate distilled under reduced pressure