4-Fluorobenzoyl chloride → Ethyl 1-(4-fluorobenzoyl)piperidine-3-carboxylate

HRID 1172727ノート

反応式

HRID 1172727 の反応式
[NH:1]1[CH2:11][CH2:10][CH2:9][CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:2]1.CCN(C(C)C)C(C)C.[F:21][C:22]1[CH:30]=[CH:29][C:25]([C:26](Cl)=[O:27])=[CH:24][CH:23]=1>C1COCC1>[CH2:7]([O:6][C:4]([CH:3]1[CH2:9][CH2:10][CH2:11][N:1]([C:26](=[O:27])[C:25]2[CH:29]=[CH:30][C:22]([F:21])=[CH:23][CH:24]=2)[CH2:2]1)=[O:5])[CH3:8]

参加物

5

反応物 3

HCID 678794-Fluorobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 98969Ethyl nipecotate

生成物 1

HCID 2905457Ethyl 1-(4-fluorobenzoyl)piperidine-3-carboxylate収率 33%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a mixture of Ethyl nipecotate (2 g, 12.72 mmol) in THF (25 ml, 0.5M) was added DIEA (4.79 ml, 27.99 mmol). The reaction mixture was cooled to 0° C. and 4-Fluoro-benzoyl chloride (2.5 g-15.76 mmol) was slowly added. The reaction was to go up to R.T and stirred for 24 h. The solution was concentrated and DCM was added following by HCl 1N. The aqueous phase was separated and organic phase was extracted twice with HCl 1N and twice with water, dried over Na2SO4, filtered and concentrated to afford 1.15 g (33%) of 1-(4-Fluoro-benzoyl)-piperidine-3-carboxylic acid ethyl ester as a colorless oil which can be used without further purification.

後処理

  1. concentrationThe solution was concentrated
  2. additionDCM was added
  3. customThe aqueous phase was separated
  4. extractionorganic phase was extracted twice with HCl 1N and twice with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-361b4862e0384bc3911ea6998ea6d09e
出典データセット
uspto-grants-2010_11
特許番号
US07834035B2

反応ノート

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