Hydrochloric Acid → 9-[2-HYDROXY-2-(4-METHOXYPHENYL)ETHYL]-2,3-DIHYDROIMIDAZO[1,2-a]BENZIMIDAZOLE HYDROCHLORIDE

HRID 54708Notes

Reaction equation

HRID 54708 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[CH:25]=[CH:24][C:8]([C:9](=[O:23])[CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]3[CH2:20][CH2:21][N:22]=[C:12]23)=[CH:7][CH:6]=1.[ClH:26]>CO>[ClH:26].[OH:23][CH:9]([C:8]1[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:25][CH:24]=1)[CH2:10][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]2[CH2:20][CH2:21][N:22]=[C:12]12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 34790182-(2,3-dihydro-9H-imidazo[1,2-a]benzimidazol-9-yl)-1-(4-methoxyphenyl)ethanoneHCID 4311764Sodium borohydride

Product 1

HCID 190408669-[2-HYDROXY-2-(4-METHOXYPHENYL)ETHYL]-2,3-DIHYDROIMIDAZO[1,2-a]BENZIMIDAZOLE HYDROCHLORIDE

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 0.3 g (7.5 mmol) of sodium borohydride bit by bit to a suspension of 2.41 g (7 mmol) of 9-(4'-methoxyphenacyl)-2,3-dihydroimidazo[1,2-a]benzimidazole--described in Example 6--in 15 ml of methanol over a period of thirty minutes at room temperature. Continue stirring for a further four hours and leave until the next day. Subsequently, add 10 ml of 10% hydrochloric acid until a pH of 2-3 is obtained, and evaporate the methanol. Treat the residue with an ammonium hydroxide solution and extract with chloroform. Recrystallise the residue. The title compound is obtained in the form of a base. Dissolve in hot ethanol and add ethereal hydrogen chloride. Allow to cool, suction-filter, and wash with ether. The title compound is obtained.

Workup

  1. customleave until the next day
  2. customis obtained
  3. customevaporate the methanol
  4. additionTreat the residue with an ammonium hydroxide solution
  5. extractionextract with chloroform
  6. customRecrystallise the residue

Sources & evidence

ORD record
ord-f008c8493abf4cd4aed29bef48d0c6e7
Source dataset
uspto-grants-1997_04
Patent number
US05623073

Reaction notes

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