Ethylamine → HCID 21835834, compound

Participants

Reaction Steps

2.70 g (6.54 mmol) of N-{2-(3,4-dimethylbenzyloxy)-ethyl}-4-(2-azidoethoxy)-3-methoxyphenylacetamide obtained in step 1 was dissolved in 100 ml of isopropanol and 1.82 ml (13.31 mmol) of ethylamine was added thereto with stirring. 66 ml(6.54 1nmol) of 1,3-propanedithiol was dissolved in isopropanol to a concentration of 0.1M, to which the solution prepared above and 2.48 g (6.54 mmol) of NaBH4 were slowly added. The resulting mixture was stirred at an ambient temperature for 1 hour and then the solvent was removed under a reduced pressure to produce a residue, which was dissolved in 10% citric acid. The resulting solution was washed with 30 ml of a mixture of ether: hexane (1:1) three times. The pH of the aqueous layer was adjusted to 12 with sodium hydroxide solution, and a saturated sodium chloride solution was added thereto. The resultant was extracted with 30 ml of dichloromethane 3 times and the organic layer was dried and concentrated under a reduced pressure to produce a solid, which was recrystallized from ethyl acetate/hexane to obtain 1.82 g (yield 72%) of the title compound as a white solid.

Provenance & Evidence