Multiple organolithium generation in the continuous flow synthesis of amitriptyline

Lukas Kupracz; Andreas Kirschning

doi:10.1002/adsc.201300614

Multiple organolithium generation in the continuous flow synthesis of amitriptyline

Lukas Kupracz, Andreas Kirschning^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Research › peer review

Abstract

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.

Original language	English
Pages (from-to)	3375-3380
Number of pages	6
Journal	Advanced Synthesis and Catalysis
Volume	355
Issue number	17
DOIs	https://doi.org/10.1002/adsc.201300614
Publication status	Published - 13 Nov 2013

Keywords

amitriptyline
antidepressants
carboxylation
flow chemistry
inductive heating
lithiation
Parham cyclization

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.201300614

Cite this

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abstract = "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.",

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N2 - 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.

AB - 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.

KW - amitriptyline

KW - antidepressants

KW - carboxylation

KW - flow chemistry

KW - inductive heating

KW - lithiation

KW - Parham cyclization

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ER -

Multiple organolithium generation in the continuous flow synthesis of amitriptyline

Abstract

Keywords

ASJC Scopus subject areas

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