Acetic Acid → 2-{[3-(4-Nitrophenyl)propyl]amino}ethan-1-ol

Participants

Reaction Steps

50 g of the previously obtained N-(2-hydroxyethyl)-3-(4-nitrophenyl)propionylamide and 31.8 g of sodium boron hydride were suspended in 500 ml of tetrahydrofuran, and 50.5 g of acetic acid was added dropwise thereto under ice cooling conditions. After completion of the addition, the solution was heated under reflux for 2 hours and then ice-cooled again, and 500 ml of water was added dropwise thereto. Afterward, 4N hydrochloric acid was added to the solution so as to adjust its pH to a level of from 5 to 6, and tetrahydrofuran was then distilled off under reduced pressure. Next, 425 ml of 4N hydrochloric acid was added to the resultant aqueous solution, and the solution was stirred at 60°-70° C. for 1 hour and then allowed to stand for cooling, so that the temperature of the solution was returned to room temperature. After washed with chloroform, the aqueous solution was adjusted to a pH of 11 by the use of a 16% aqueous sodium hydroxide solution, and extraction was carried out twice with 500 ml of chloroform. The chloroform extracts were joined and concentrated under reduced pressure, and the resultant residue was crystallized from 900 ml of toluene to obtain 38.6 g of crystalline N-(2-hydroxyethyl)-3-(4-nitrophenyl)propylamine, which had a melting point of from 82.5° to 84.5° C.

Provenance & Evidence