ChemicalBook CAS DataBase List Clomifene

Clomifene synthesis

4synthesis methods

Product Name:Clomifene
CAS Number:911-45-5
Molecular formula:C26H28ClNO
Molecular Weight:405.96

Clomifene, 2-[p-(2-chloro-1,2-diphenylvinyl)phenoxy]triethylamine (28.2.4), is synthesized from 4-hydroxybenzophenone by reacting it with 2-diethylaminoethylchloride in the presence of an alkali, which gives 4-(2-diethylaminoethoxy)benzophenone (28.2.1). This is reacted with benzylmagnesium chloride in a Grignard reaction, forming as a result the corresponding carbinol (28.2.2). Dehydrating this with hydrogen chloride gives 2-[p-(1,2-diphenylvinyl) phenoxy]triethylamine (28.2.4), the vinylic hydrogen atom of which is replaced with a chlorine atom using N-chlorosuccinimide, giving clomifene (28.2.4) .

alpha-[4-[2-(diethylamino)ethoxy]phenyl]-alpha-phenylphenethyl alcohol

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Yield:-

Steps:

Multi-step reaction with 2 steps
1.1: sulfuric acid / dichloromethane / 1 h / 0 - 20 °C
2.1: N-chloro-succinimide / dichloromethane / 32 h / 20 °C
2.2: 0.5 h / 20 °C / pH 8 - 9

References:

US2017/73302,2017,A1