Reaction #1030

Reaction equation

cis-N-(1-ethoxycarbonyl-3-methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide

potassium hydroxide

water

→

title compound

Yield 16.3%

cis-N-(3-Methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide

Yield 16.3%

Solvents

2-propanol

Conditions

Workup

1. 1
   TemperatureThe obtained solution was refluxed for 1.5 hours
2. 2
   Temperaturecooled
3. 3
   workup.ADDITIONfollowed by the addition
4. 4
   ExtractionThe resulting mixture was extracted with 10% 2-propanol/chloroform thrice
5. 5
   DryingThe combined organic phases were dried over magnesium sulfate
6. 6
   OtherThe residue was purified by silica gel column chromatography (5 to 12% methanol/dichloromethane)

Procedure

2.50 g of the cis-N-(1-ethoxycarbonyl-3-methoxy-4-piperidinyl)-4-amino-5-chloro-2-((S)-1-methyl-2-butynyl)oxybenzamide prepared in the Example 7 and 4.5 g of potassium hydroxide were dissolved in 2-propanol. The obtained solution was refluxed for 1.5 hours and cooled, followed by the addition thereto of water. The resulting mixture was extracted with 10% 2-propanol/chloroform thrice. The combined organic phases were dried over magnesium sulfate and freed from the solvent. The residue was purified by silica gel column chromatography (5 to 12% methanol/dichloromethane) to give 0.34 g of the title compound.

Source