Potassium Carbonate → rac Bepotastine Ethyl Ester

HRID 1651559Notes

Reaction equation

HRID 1651559 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH: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]([CH: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 111411972-((4-Chlorophenyl)(4-piperidinyloxy)methyl)pyridine

Product 1

HCID 3079389rac Bepotastine Ethyl EsterYield 91.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

After 4.98 g (16.45 mmol) of 4-[(4-chlorophenyl)-2-pyridylmethoxy]piperidine and 3.85 g (19.74 mmol) of ethyl 4-bromobutanoate were dissolved in 35 ml of acetone, 2.73 g (19.75 mmol) of potassium carbonate was added to the mixed solution, and the mixture was stirred under reflux by heating for 4 hours. The insolubles were filtered off, and the filtrate was concentrated under reduced pressure. The residue was separated by silica gel column chromatography using a solvent mixture of chloroform and methanol in the volume ratio of 30:1 as an eluent. The desired fraction was concentrated under reduced pressure to give 6.26 g (91%) of ethyl 4-[4-[(4-chlorophenyl)-2-pyridylmethoxy]-1-piperidyl]-butanoate as an oil.

Workup

  1. temperatureunder reflux
  2. temperatureby heating for 4 hours
  3. filtrationThe insolubles were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was separated by silica gel column chromatography
  6. additiona solvent mixture of chloroform and methanol in the volume ratio of 30:1 as an eluent
  7. concentrationThe desired fraction was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a1d587fdd09c4a6586a4ddd10cb479e8
Source dataset
uspto-grants-1990_05
Patent number
US04929618

Reaction notes

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