4-Carbethoxy-3-methyl-2-cyclohexen-1-one → 2-Methyl-4-oxo-3-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-cyclohex-2-enecarboxylic acid ethyl ester

HRID 351450

反応式

HRID 351450 の反応式
CC([O-])(C)C.[K+].[CH3:7][CH2:8][O:9][C:10]([CH:12]1[C:18]([CH3:19])=[CH:17][C:15](=[O:16])[CH2:14][CH2:13]1)=[O:11].Cl.Cl[CH2:22][C:23]1[CH:37]=[CH:36][C:26]([O:27][CH2:28][CH2:29][N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:25][CH:24]=1>>[CH2:8]([O:9][C:10]([CH:12]1[CH2:13][CH2:14][C:15](=[O:16])[C:17]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:36][CH:37]=2)=[C:18]1[CH3:19])=[O:11])[CH3:7]

参加物

4

反応物 3

HCID 790204-Carbethoxy-3-methyl-2-cyclohexen-1-oneHCID 98607851-(2-(4-(Chloromethyl)phenoxy)ethyl)piperidine hydrochlorideHCID 23665647Potassium tert-butoxide

生成物 1

HCID 694292272-Methyl-4-oxo-3-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-cyclohex-2-enecarboxylic acid ethyl ester

反応条件

温度
25 °C

実験手順

To the solution of KOtBu (1.0 M in tBuOH, 10.7 mL) at 25 cC was added Hagemann's ester (1.0 mL, 5.324 mmol). The mixture was stirred for 10 min at 25° C. and then to the mixture was added 1-[2-(4-chloromethyl-phenoxy)ethyl]piperidine hydrochloride (1.54 g, 5.324 mmol). The mixture was refluxed for 3 h. The tBuOH was distilled off, then the reaction mixture was diluted with water and diethyl ether. The layers were separated and the aqueous layer was extracted with diethyl ether. The organic extracts were acidified with 1N HCl (100 mL). The layers were separated and the diethyl ether layer was discarded. The aqueous layer was then basicified to pH 11 with 10% NaOH (aq) and extracted with diethyl ether to yield 2-methyl-4-oxo-3-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-cyclohex-2-enecarboxylic acid ethyl ester as dark amber oil.

後処理

  1. temperatureThe mixture was refluxed for 3 h
  2. distillationThe tBuOH was distilled off
  3. additionthe reaction mixture was diluted with water and diethyl ether
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with diethyl ether
  6. customThe layers were separated
  7. extractionextracted with diethyl ether

出典と根拠

ORDレコード
ord-a4b150d8a0bb47e0a240ae5c979efb25
出典データセット
uspto-grants-2007_02
特許番号
US07183445B2

関連ノート

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