Reaction #2146771

Reaction equation

azepan-4-ol

sodium hydride

6-fluoro-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one

water

6-fluoro-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one

azepan-4-ol

sodium hydride

→

6-(azepan-4-yloxy)-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one

Yield 41.0%

Solvents

dimethylacetamide

dimethylacetamide

Conditions

Workup

1. 1
   Otherwas obtained
2. 2
   Otherwas isolated by filtration
3. 3
   Otherdried overnight in vacuum

Procedure

A solution of 58 mg (0.51 mmol) azepan-4-ol in 5 ml dimethylacetamide was stirred with 45 mg (1.52 mmol) 80 percent sodium hydride for 45 minutes at room temperature. Then 150 mg (0.51 mmol) 6-fluoro-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one in dimethylacetamide was added. The reaction mixture was heated to 80° C. for 3 days during which additional amounts of azepan-4-ol and sodium hydride were added until complete conversion of the 6-fluoro-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one was obtained. The reaction mixture was slowly added to 10 ml water and after 1 h of stirring the product was isolated by filtration and dried overnight in vacuum. 82 mg of 6-(azepan-4-yloxy)-2-(4-methoxy-benzyl)-7-methyl-2H-isoquinolin-1-one were obtained.

Source