Diisopropylethylamine → HCID 131723694, compound

Participants

Reaction Steps

Ethyldiisopropylamine (0.3 ml) was added at ambient temperature to a solution of 4-chloro-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-isophthalamic acid (0.15 g, Example 60a), piperazine-1-carboxylic acid tert-butyl ester (0.16 g) and PyBrOP (0.40 g) in N-methylpyrrolidinone (10 ml). After 5 h the reaction mixture was diluted with ethyl acetate and washed twice with water, twice with 10% KHSO4 solution, twice with saturated NaHCO3 solution and once with brine, then dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (eluting with ethanol (0-5%) in dichloromethane), then redissolved in methanol (10 ml) and treated with hydrochloric acid (4N dioxane, 1 ml). After 48 h the reaction mixture was concentrated under reduced pressure and recrystallised from iso-hexaxne/propan-2-ol to yield the title compound as a solid (0.10 g).

Provenance & Evidence