Potassium Carbonate → rac Bepotastine Ethyl Ester

HRID 1651559

反応式

HRID 1651559 の反応式
[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

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 111411972-((4-Chlorophenyl)(4-piperidinyloxy)methyl)pyridine

生成物 1

HCID 3079389rac Bepotastine Ethyl Ester収率 91.3%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a1d587fdd09c4a6586a4ddd10cb479e8
出典データセット
uspto-grants-1990_05
特許番号
US04929618

関連ノート

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