Hydrochloric Acid → 1-{2-[4-((5-Fluoro-3-indolyl)methyl)piperidino]ethyl}-2H-benzimidazolin-2-one

HRID 1196613Notes

Reaction equation

HRID 1196613 reaction equation
Cl.C([N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][C:23]3[C:31]4[C:26](=[CH:27][CH:28]=[C:29]([F:32])[CH:30]=4)[NH:25][CH:24]=3)[CH2:18][CH2:17]2)[C:6]1=[O:33])(C)=C.ClCCl>C(O)C>[F:32][C:29]1[CH:30]=[C:31]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[CH2:22][CH:19]1[CH2:18][CH2:17][N:16]([CH2:15][CH2:14][N:7]2[C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:5][C:6]2=[O:33])[CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 198988863-isopropenyl-1-{2-[4-((5-fluoro-3-indolyl)methyl)piperidino]ethyl}-2H-benzimidazol-2-one

Product 1

HCID 198988981-{2-[4-((5-Fluoro-3-indolyl)methyl)piperidino]ethyl}-2H-benzimidazolin-2-oneYield 11%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

6N hydrochloric acid (9.3 cc) is introduced at a temperature in the region of 20° C. into a solution of 3-isopropenyl-1-{2-[4-((5-fluoro-3-indolyl)methyl)piperidino]ethyl}-2H-benzimidazol-2-one (4 g) in ethanol (50 cc). The solution is heated to boiling for 1 hour and then cooled to a temperature in the vicinity of 20° C. The reaction medium is taken up with dichloromethane (100 cc) and distilled water (30 cc) and alkalinized to pH 9 with 5N sodium hydroxide. The organic phase is extracted with dichloromethane (3×30 cc), washed with distilled water (90 cc), dried over anhydrous magnesium sulphate, treated with vegetable charcoal, filtered and concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is recrystallized in methyl ethyl ketone (15 cc). 1-{2-[4-((5-Fluoro-3-indolyl)methyl)piperidino]ethyl}-2H-benzimidazolin-2-one (0.4 g), m.p. 220° C., is obtained.

Workup

  1. temperatureThe solution is heated
  2. distillationdistilled water (30 cc)
  3. extractionThe organic phase is extracted with dichloromethane (3×30 cc)
  4. washwashed with distilled water (90 cc)
  5. dry with materialdried over anhydrous magnesium sulphate
  6. additiontreated with vegetable charcoal
  7. filtrationfiltered
  8. concentrationconcentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)
  9. customThe residue is recrystallized in methyl ethyl ketone (15 cc)

Sources & evidence

ORD record
ord-38c414d613044e2c83d66e84b7c95dc8
Source dataset
uspto-grants-1992_05
Patent number
US05114949

Reaction notes

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