Hydrochloric Acid → HCID 13272340, compound

HRID 1742818Notes

Reaction equation

HRID 1742818 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[CH2:2]2.C(O)(=O)[C@H]([C@@H](C(O)=O)O)O.[OH-].[Na+].Cl>CO.O.CC(C)=O>[ClH:17].[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@H:3]([NH:9][C:10](=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[CH2:2]2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 439655D-Tartaric acidHCID 28025403-Chloro-N-(3-quinuclidinyl)benzamide

Product 1

HCID 13272340HCID 13272340, compoundYield 87.1%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

In 60 ml of methanol was dissolved 23 g of N-(3-quinuclidinyl)-3-chlorobenzamide followed by addition of a solution of D-(-)-tartaric acid (13 g) in 40 ml of methanol. The mixture was ice-cooled and the resulting crystals were recovered by filtration. To the crystals was added 350 ml of methanol and the mixture was refluxed for a while. After cooling, the crystals were collected by filtration. The above operation was repeated twice and the crystals obtained were dissolved in water and sodium hydroxide solution was added. This mixture was extracted with chloroform and the extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was then evaporated off to obtain a colorless oil. This oil was treated with ethanolic hydrochloric acid in acetone and the precipitated hydrochloride was recovered by filtration to give 11.4 g of the desired compound as white crystals. m.p. 244°-246° C.

Workup

  1. temperaturecooled
  2. filtrationthe resulting crystals were recovered by filtration
  3. additionTo the crystals was added 350 ml of methanol
  4. temperaturethe mixture was refluxed for a while
  5. temperatureAfter cooling
  6. filtrationthe crystals were collected by filtration
  7. customthe crystals obtained
  8. extractionThis mixture was extracted with chloroform
  9. washthe extract was washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was then evaporated off
  12. customto obtain a colorless oil
  13. filtrationthe precipitated hydrochloride was recovered by filtration

Sources & evidence

ORD record
ord-d5e28e8fa6944c4498e6657fb12ddb87
Source dataset
uspto-grants-1994_08
Patent number
US05342845

Reaction notes

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