Reaction #11441

Reaction equation

tert-butyl 4-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butylcarbamate

trifluoroacetic acid

sodium hydroxide

→

4-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butylamine

Yield 87.8%

Solvents

dichloromethane

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Temperaturea chilled
2. 2
   ConcentrationThe reaction mixture was concentrated under reduced pressure
3. 3
   Otherto provide a brown oil
4. 4
   OtherThe layers were separated
5. 5
   Extractionthe aqueous layer was extracted with dichloromethane
6. 6
   Dryingdried over magnesium sulfate
7. 7
   Concentrationconcentrated under reduced pressure

Procedure

A solution of tert-butyl 4-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butylcarbamate (6.70 g, 15.8 mmol) in dichloromethane (50 mL) was slowly added to a chilled (0° C.) mixture of trifluoroacetic acid (60 mL) and dichloromethane (100 mL). The reaction mixture was allowed to warm to ambient temperature and then left overnight. The reaction mixture was concentrated under reduced pressure to provide a brown oil. The oil was dissolved in dichloromethane and the solution was made basic (pH 14) with 5% aqueous sodium hydroxide. The layers were separated and the aqueous layer was extracted with dichloromethane. The organic layers were combined, dried over magnesium sulfate and then concentrated under reduced pressure to provide 4.50 g of 4-(2,6,7-trimethyl-4-phenoxy-1H-imidazo[4,5-c]pyridin-1-yl)butylamine as a brown oil.

Source