Reaction #73484

Reaction equation

acetonitrile water

Hydrochloric acid

1-[4-(7-chloro-1-methoxyisoquinolin-6-yloxy)-cyclohexyl]-1-(4-methoxyphenyl)-ethylamine

→

desired product

Yield 97.0%

6-{4-[1-Amino-1-(4-methoxy-phenyl)-ethyl]-cyclohexyloxy}-7-chloro-2H-isoquinolin-1-one

Yield 97.0%

Solvents

isopropanol

Conditions

Workup

1. 1
   OtherIsopropanol was removed under reduced pressure
2. 2
   Otherthe remaining aqueous solution freeze dried
3. 3
   Otherto give crude product as an amorphous powder
4. 4
   Otherdried

Procedure

Hydrochloric acid (0.4 mL of a 1M aqueous solution) was added to a solution of 1-[4-(7-chloro-1-methoxyisoquinolin-6-yloxy)-cyclohexyl]-1-(4-methoxyphenyl)-ethylamine (109, 30 mg, 0.07 mmol) in isopropanol (0.4 mL). The reaction mixture was heated in a microwave oven at 100° C. for 30 minutes. Isopropanol was removed under reduced pressure and the remaining aqueous solution freeze dried to give crude product as an amorphous powder. This was treated twice with acetonitrile/water and freeze dried to give 29 mg of the desired product Example 117 as a colourless hydrochloride salt. Rt=2.60 min (Method 2). Detected mass: 410.1 (M—NH3+H+).

Source