Chloroacetyl chloride → N-(1-Benzyl-piperidin-4-yl)-2-chloro-N-isopropyl-acetamide

HRID 659079ノート

反応式

HRID 659079 の反応式
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH:15]([CH3:17])[CH3:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Cl:27][CH2:28][C:29](Cl)=[O:30]>ClCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH:15]([CH3:17])[CH3:16])[C:29](=[O:30])[CH2:28][Cl:27])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 107283101-Benzyl-N-isopropylpiperidin-4-amine

生成物 1

HCID 66565165N-(1-Benzyl-piperidin-4-yl)-2-chloro-N-isopropyl-acetamide収率 50.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

To a mixture of 1-benzyl-4-(isopropylamino)piperidine (8 g, 34.45 mmol) and DIPEA (7.2 mL, 41.3 mmol) in 200 mL of dichloromethane was added dropwise a solution of 2-chloroacetyl chloride (3.01 mL, 37.9 mmol) in dichloromethane (400 mL) at 0° C. The reaction mixture was stirred at 0° C. for 15 min and then at room temperature for 2 h. The reaction mixture was then washed with saturated sodium bicarbonate, brine, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was purified by flash column chromatography (ethyl acetate/hexane/triethylamine: 42.5/56.5/1) to give 5.35 g of the title intermediate as a viscous oil (50% yield).

後処理

  1. waitat room temperature for 2 h
  2. washThe reaction mixture was then washed with saturated sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by flash column chromatography (ethyl acetate/hexane/triethylamine: 42.5/56.5/1)

出典と根拠

ORDレコード
ord-64ceaa9e27b34369b9ec8a7b788eef19
出典データセット
uspto-grants-2011_12
特許番号
US08080565B2

反応ノート

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