Reaction #46898

Reaction equation

1-cyclopropyl-piperidin-4-ylamine dihydrochloride

NaHCO3

2-trichloromethyl-1H-benzoimidazole-5-carboxylic acid methyl ester

→

2-(1-cyclopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-5-carboxylic methyl ester

Solvents

THF

water

THF

Conditions

Workup

1. 1
   workup.ADDITIONwas added
2. 2
   OtherThe THF was evaporated
3. 3
   FiltrationThe precipitate was filtered off
4. 4
   workup.ADDITIONtreated twice with about 300 mL of a saturated NaHCO3-solution under ultrasonic conditions
5. 5
   FiltrationAfter filtration the resulting solid
6. 6
   Washwas washed twice with 150 mL water
7. 7
   Otherdried under reduced pressure at 45° C.

Procedure

To a mixture of 7.53 g (35.3 mmol) 1-cyclopropyl-piperidin-4-ylamine dihydrochloride and 32.39 g (0.386 mol) NaHCO3 in 1300 mL THF and 370 mL water a solution of 11.79 g (32.1 mmol) 2-trichloromethyl-1H-benzoimidazole-5-carboxylic acid methyl ester in 360 mL THF was added. The reaction mixture was stirred vigorously for 2 h at RT. The THF was evaporated. The precipitate was filtered off and treated twice with about 300 mL of a saturated NaHCO3-solution under ultrasonic conditions. After filtration the resulting solid was washed twice with 150 mL water and dried under reduced pressure at 45° C. to give pure 2-(1-cyclopropyl-piperidin-4-ylcarbamoyl)-1H-benzoimidazole-5-carboxylic methyl ester in form of a light brown crystalline material.

Source