Triethylamine → HCID 23453182, compound

Participants

Reaction Steps

5.4 g of 2-aminomethyl-2-hydroxymethyl-3,4,5-trihydroxypiperidine are dissolved in 50 ml of a methanol/water mixture (1:1), and 3.92 ml of triethylamine and, at -5° C., 5.44 g of 4-nitrobenzoyl chloride are added. The mixture is stirred for 24 hours and evaporated in vacuo, the residue is taken up in ether/water and the phases are separated. The aqueous phase is extracted once with ether and the product phase is then evaporated. The residue is dissolved in a little water and the solution is discharged onto a column 120 cm long and 4 cm wide which contains cellulose as the stationary phase and 99% pure acetone as the mobile phase. The column is eluted successively with 99% pure acetone, 95% pure acetone and finally 90% pure acetone. The individual fractions are examined by thin layer chromatography to determine their content of the required compound. The fractions containing the desired product are collected and evaporated. 2.6 g of 2-(4-nitrobenzoylaminomethyl)-2-hydroxymethyl-3,4,5 -trihydroxypiperidine are obtained.

Provenance & Evidence