Triethylamine → HCID 13361842, compound

Participants

Reaction Steps

5.4 g of 6-hydroxy-1,2,3,4-tetrahydroisoquinoline are acylated twice with 14.2 g of 4-methoxydihydrocinnamoyl chloride in methylene chloride in the presence of 7.5 g of triethylamine, the mixture is extracted by shaking with water, and the organic phase is dried and evaporated in a rotary evaporator. The crude product is dissolved, without further purification, in tetrahydrofuran, and added dropwise, with cooling, to a solution of 1.5 g of lithium aluminum hydride in dry tetrahydrofuran. After destroying the reagent with water, inorganic material is filtered off and the filtrate is dried. The residue from filtration is dried, extracted twice by boiling with methanol, and the methanol and tetrahydrofuran are evaporated together in a rotary evaporator. After triturating the oily residue with ethyl acetate, 3.5 g of colorless product (33% of theory) are obtained. Melting point: 163°-164°.

Provenance & Evidence