Réaction #2396836

Équation de réaction

2-amino-N-[4-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]-butyl]benzamide

1,1'-carbonylbis[1H-imidazole]

→

3-[4-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]butyl]-2,4(1H,3H)-quinazolinedione

Rendement 35.5%

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Températurerefluxed overnight
2. 2
   AutreThe reaction mixture was evaporated
3. 3
   AutreThe residue was purified by column chromatography over silica gel using first
4. 4
   workup.ADDITIONa mixture of trichloromethane and methanol saturated with ammonia (97:3 by volume)
5. 5
   workup.ADDITIONa mixture of trichloromethane and methanol saturated with ammonia (95:5 by volume) as eluent
6. 6
   AutreThe pure fractions were collected
7. 7
   Autrethe eluent was evaporated
8. 8
   AutreThe residue was crystallized from 2-propanone

Mode opératoire

A mixture of 10.3 parts of 2-amino-N-[4-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]-butyl]benzamide, 3.2 parts of 1,1'-carbonylbis[1H-imidazole] and 180 parts of tetrahydrofuran was stirred and refluxed overnight. The reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using first a mixture of trichloromethane and methanol saturated with ammonia (97:3 by volume) and then a mixture of trichloromethane and methanol saturated with ammonia (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from 2-propanone, yielding 3.8 parts (35.5%) of 3-[4-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]butyl]-2,4(1H,3H)-quinazolinedione; mp. 187.3° C. (489).

Source