Hydrochloric Acid → HCID 13272340, compound

HRID 2254841Notes

Reaction equation

HRID 2254841 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.Cl>CO.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

6

Reactant 3

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

Product 1

HCID 13272340HCID 13272340, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent2×

Procedure

N-(3-Quinuclidinyl)-3-chlorobenzamide (52.5 g) dissolved in methanol is added to a solution of D-tartaric acid (29.7 g) in methanol. The precipitate obtained is collected by filtration and treated twice with methanol under reflux. The salt thus purified (20 g) is decomposed with aqueous sodium hydroxide solution and the product extracted with chloroform. After the organic phase has been dried and evaporated, the base obtained is treated in acetone with ethanolic hydrogen chloride solution. The hydrochloride which precipitates is collected by filtration and recrystallized in ethanol. 9.4 g of optically pure (S)-(-)-N-(3-quinuclidinyl)-3-chlorobenzamide hydrochloride are obtained.

Workup

  1. customThe precipitate obtained
  2. filtrationis collected by filtration
  3. additiontreated twice with methanol
  4. temperatureunder reflux
  5. customThe salt thus purified (20 g)
  6. extractionthe product extracted with chloroform
  7. customAfter the organic phase has been dried
  8. customevaporated
  9. customthe base obtained
  10. customThe hydrochloride which precipitates
  11. filtrationis collected by filtration
  12. customrecrystallized in ethanol

Sources & evidence

ORD record
ord-cfe808db756e4fe4a15a521a70df74b6
Source dataset
uspto-grants-1993_08
Patent number
US05237066

Reaction notes

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