Potassium Carbonate → Bepotastine Ethyl Ester

HRID 1180646Notes

Reaction equation

HRID 1180646 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[O:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.Br[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[O:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 108920052-((4-Chlorophenyl)(piperidin-4-yloxy)methyl)pyridine, (S)-

Product 1

HCID 15055867Bepotastine Ethyl EsterYield 93.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In 15 ml of acetone was dissolved 1.33 g (4.39 mmol, optical purity: 99.4% e.e.) of (S)-(−)-4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidine obtained according to Reference example 1, then, 1.03 g (5.28 mmol) of ethyl 4-bromobutanoate and 0.73 g (5.28 mmol) of potassium carbonate were added, and the mixture was refluxed under stirring for 7 hours. Insolubles were filtered off and the filtrate was concentrated under reduced pressure. The resulting slightly yellowish oily product was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol (volume ratio: 30:1) as an eluent. Fractions containing the isolated objective compound were concentrated under reduced pressure to afford 1.71 g of ethyl (S)-4-[4-[(4-chlorophenyl)(2-pyridyl)methoxy]piperidino]-butanoate as an oily product (Yield: 93.4%, optical purity: 99.4% e.e.).

Workup

  1. customobtained
  2. temperaturethe mixture was refluxed
  3. filtrationInsolubles were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting slightly yellowish oily product was purified by silica gel column chromatography
  6. additionFractions containing the isolated objective compound
  7. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-5671828476074fb298a5afbb802ff2fa
Source dataset
uspto-grants-2007_10
Patent number
US07282589B2

Reaction notes

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