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Multiple Organolithium Generation in the Continuous Flow Synthesis of Amitriptyline
Author(s) -
Kupracz Lukas,
Kirschning Andreas
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300614
Subject(s) - chemistry , continuous flow , amitriptyline , carboxylation , tricyclic , flow chemistry , combinatorial chemistry , protocol (science) , organic chemistry , biochemical engineering , pharmacology , catalysis , medicine , alternative medicine , pathology , engineering
A continuous flow protocol for the preparation of the tricyclic antidepressant (TCA) amitriptyline is reported. The advantages of flow chemistry when handling organometallic agents as well as when performing reaction with gases are demonstrated. Continuous multilithiation combined with carboxylation and the Parham cyclization, a Grignard addition and thermolytic water elimination by inductive heating are key features of the multistep protocol.