Benzylamine → HCID 54469074, compound

Participants

Reaction Conditions

Reaction Steps

To 44.7 g (0.15 mol) of the (2S,3R)-2,3-epoxyoctadecanoic acid (V-2) obtained in (4) above were added 150 ml of water and 1.6 g (4 mmol) of a phase transfer catalyst Aliquat 336 at room temperature, followed by stirring at 2 to 3° C. To the mixture was added dropwise 48.2 g (0.45 mol) of benzylamine (VI), followed by further stirring for about 5 minutes. To the mixture was added 24.0 ml (0.12 mol) of a 5N sodium hydroxide aqueous solution, and the mixture was refluxed for 2 hours and then stirred at room temperature for 16 hours. The reaction mixture was cooled to 0 to 5° C., 6.0 ml (0.03 mol) of a 5N sodium hydroxide aqueous solution was added thereto, and the mixture was extracted with 800 ml of diisopropyl ether. The aqueous layer was adjusted to pH 5 to 6 with 2N hydrochloric acid aqueous solution, and the precipitated white crystals were extracted with 1600 ml of diisopropyl ether and collected by filtration under ice-cooling to obtain 55.3 g (0.137 mol; yield: 91.0%) of the title compound (melting point: 132° C.).

Provenance & Evidence