Benzoic Acid → (s)-4-[4-[(4-Chlorophenyl)(2-pyridyl)methoxy]piperidino]butanoic acid monobenzoic acid salt

HRID 1180649Notes

Reaction equation

HRID 1180649 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[O:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:12][CH2:11]2)=[CH:4][CH:3]=1.[C:28]([OH:36])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CC(C)=O>[C:28]([OH:36])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[O:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:12][CH2:11]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 243Benzoic AcidHCID 164522Bepotastine

Product 1

HCID 67541632(s)-4-[4-[(4-Chlorophenyl)(2-pyridyl)methoxy]piperidino]butanoic acid monobenzoic acid saltYield 72.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 30 ml of acetone was dissolved 0.91 g (2.34 mmol) of (S)-4-[4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidino]-butanoic acid obtained according to Example 1, and then, 0.29 g (2.37 mmol) of benzoic acid was added to the solution and the mixture was made uniform. Then, the mixture was concentrated under reduced pressure. To the residue was added 50 ml of isopropyl ether and the mixture was allowed to stand for two days, part of the syrupy product was crystallized. When the material was stirred by a spatula and further allowed to stand, whole parts were crystallized. This crystals were recrystallized from 36 ml of ethyl acetate to afford 0.87 g (Yield: 72.8%, optical purity: 99.4% e.e.) of the desired product as white powder crystals.

Workup

  1. customobtained
  2. concentrationThen, the mixture was concentrated under reduced pressure
  3. additionTo the residue was added 50 ml of isopropyl ether
  4. custompart of the syrupy product was crystallized
  5. customwhole parts were crystallized
  6. customThis crystals were recrystallized from 36 ml of ethyl acetate

Sources & evidence

ORD record
ord-b52a38c887324034a5f9f1c940c76f4e
Source dataset
uspto-grants-2007_10
Patent number
US07282589B2

Reaction notes

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