Hydrochloric Acid → HCID 20342607, compound

HRID 2050371Notes

Reaction equation

HRID 2050371 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([C:12](=[O:30])[CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[NH:22][C:21]3=[O:29])[CH2:16][CH2:15]2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[BH4-].[Na+].C(=O)(O)[O-].[Na+].[ClH:38]>CO.C(O)(=O)C>[ClH:38].[OH:1][C:2]1[CH:11]=[CH:10][C:9]([CH:12]([OH:30])[CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[NH:22][C:21]3=[O:29])[CH2:16][CH2:15]2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 20342608HCID 20342608, compound

Product 1

HCID 20342607HCID 20342607, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

The methyl 2-hydroxy-5-[4-(2-oxo-1-benzimidazolinyl)piperidinoacetyl]benzoate is dissolved in one liter of methanol and cooled in an ice-methanol bath. Sodium borohydride (7.44 g) is added in portions over a period of 25 minutes. The mixture is stirred for approximately 30 minutes and poured onto one liter of ice-water. The mixture is acidified with 500 ml of a 10% acetic acid solution made basic by the addition of sodium bicarbonate and extracted with methylene chloride. The combined extracts are washed with water, dried over MgSO4 which is removed by filtration, and the filtrate evaporated in vacuo leaving a residue of 11.3 g, having a m.pt. of 211°-13° C. (dec.). The residue is dissolved in one equivalent of methanolic hydrogen chloride and precipitated from solution with diethyl ether. Recrystallization of the precipitate from methanol yields methyl 2-hydroxy-5-[1-hydroxy-2-[4-(2-oxo-1-benzimidazolinyl)piperidino]ethyl]benzoate hydrochloride having a m.pt. of 229°-30° C. (dec.).

Workup

  1. temperaturecooled in an ice-methanol bath
  2. extractionextracted with methylene chloride
  3. washThe combined extracts are washed with water
  4. dry with materialdried over MgSO4 which
  5. customis removed by filtration
  6. customthe filtrate evaporated in vacuo
  7. customleaving a residue of 11.3 g
  8. customprecipitated from solution with diethyl ether
  9. customRecrystallization of the precipitate from methanol

Sources & evidence

ORD record
ord-2b3471f2511947248099205045ef2876
Source dataset
uspto-grants-1980_04
Patent number
US04200755

Reaction notes

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