HCID 14210634, compound → HCID 14210635, compound

HRID 1762121Notes

Reaction equation

HRID 1762121 reaction equation
C([O:3][C:4](=O)[NH:5][C:6]1[C:11]([CH:12]2[CH2:17][CH2:16][CH2:15][N:14](C(=O)C(F)(F)F)[CH2:13]2)=[CH:10][CH:9]=[CH:8][C:7]=1[NH2:24])C>CO.O.[OH-].[K+]>[NH:14]1[CH2:15][CH2:16][CH2:17][CH:12]([C:11]2[C:6]3[NH:5][C:4](=[O:3])[NH:24][C:7]=3[CH:8]=[CH:9][CH:10]=2)[CH2:13]1

Participants

5

Reactant 1

HCID 14210634HCID 14210634, compound

Product 1

HCID 14210635HCID 14210635, compoundYield 50.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14797Potassium HydroxideSolvent

Procedure

4 g of the product of Step E in 80 ml of methanol, 16 ml of water and 16 ml of potassium hydroxide were taken to 80° C. for 4 hours with stirring under an inert atmosphere. After evaporating the methanol under reduced pressure, adding 30 ml of water, adjusting the pH to 6-8 by acetic acid and taking to dryness under reduced pressure, the residue was purified by chromatography on silica, (eluent: methylene chloride-methanol-triethylamine (6-3-1) to obtain 2.15 g of crude product. The latter was triturated in ethyl ether, separated, dried and crystallized from ethanol to obtain 1.23 g of 1,3-dihydro-4-(3-piperidinyl)-2H-benzimidazol-2-one melting at about 260° C.

Workup

  1. customAfter evaporating the methanol under reduced pressure
  2. additionadding 30 ml of water
  3. customthe residue was purified by chromatography on silica
  4. custom(eluent: methylene chloride-methanol-triethylamine (6-3-1) to obtain 2.15 g of crude product
  5. customThe latter was triturated in ethyl ether
  6. customseparated
  7. customdried
  8. customcrystallized from ethanol

Sources & evidence

ORD record
ord-4eeb3d0d5cfd42c3b3156311e74e49dc
Source dataset
uspto-grants-1989_05
Patent number
US04831043

Reaction notes

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