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ChemicalBook CAS DataBase List Maprotiline
10262-69-8

Maprotiline synthesis

4synthesis methods
Maprotiline, N-methyl-9,10-ethanoanthracen-9(10H)-propylamine (7.1.22), is synthesized by a 42 cycloaddition reaction of 9-(3-methylaminopropyl)anthracene with ethylene [39–41].


Maprotiline is frequently referred to as a tetracyclic antidepressant. This “hybrid” drug, containing both elements of “classic tricyclic antidepressants” and protriptyline elements, is pharmacologically and clinically more similar to imipramine.
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Yield:-

Steps:

Multi-step reaction with 6 steps
1: (i) KOtBu, tBuOH, (ii) aq. HCl
2: Zn, aq. NH3
3: dimethylformamide / 170 °C
4: (COCl)2
6: LiAlH4 / diethyl ether

References:

Wilhelm;Schmidt [Helvetica chimica acta,1969,vol. 52,# 6,p. 1385 - 1395]

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