ChemicalBook CAS DataBase List 3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl]isoquinoline

3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl]isoquinoline synthesis

4synthesis methods

Product Name:3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl]isoquinoline
CAS Number:51072-35-6
Molecular formula:C17H21NO
Molecular Weight:255.35

N-[2-(1-cyclohexen-1-yl)ethyl]-2-(4-methoxyphenyl)acetamide

51072-34-5
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3,4,5,6,7,8-hexahydro-1-[(4-methoxyphenyl)methyl]isoquinoline

51072-35-6
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Yield:51072-35-6 97%

Reaction Conditions:

with trichlorophosphate in toluene; for 4 h;Reflux;

Steps:

1.2 (2) Preparation of 1- (4-methoxy) benzyl-3,4,5,6,7,8-hexahydroisoquinoline (V)

A 500 ml three-necked round bottom flask was charged with N- (2- (1-en-1-cyclohexyl) ethyl) -2- p- methoxyphenylacetamide (IV) (50.0 g, 182.9 mmol) , Toluene (200 ml) and phosphorus oxychloride (35 ml) were added and the mixture was heated to reflux for 4 h in an oil bath. The reaction was completed. The mixture was cooled to room temperature and the toluene recovered under reduced pressure. The residue was slowly poured into water (200 ml) and extracted with methylene chloride (3x100 ml). The organic layer was washed with water (2x60 ml) and brine (60 ml) Sodium was dried, filtered and concentrated to afford 45.67 g of 1- (4-methoxy) benzyl-3,4,5,6,7,8-hexahydroisoquinoline (V) in 97.0% yield.

References:

CN104119273,2017,B Location in patent:Paragraph 0177; 0180; 0181

30356-08-2 Synthesis