Ethyl 4-amino-1-piperidinecarboxylate → (1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonyl-piperidin-4-yl)amine

HRID 323183

反応式

HRID 323183 の反応式
[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1Cl)[CH3:2].[NH2:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:19][CH2:18]1>C(OCC)(=O)C.CCCCCC>[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH:16][CH:17]1[CH2:18][CH2:19][N:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:21][CH2:22]1)[CH3:2]

参加物

4

反応物 2

HCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 104893562-chloro-1-(2-ethoxyethyl)-1H-benzimidazole

生成物 1

HCID 22009481(1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonyl-piperidin-4-yl)amine

試薬・触媒・溶媒 1

HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
170 °C

実験手順

Combine 1-(2-ethoxyethyl)-2-chloro-1H-benzimidazole (3.06 g, 13.62 mmol) and ethyl 4-aminopiperidine-1-carboxylate (5.16 g, 30 mmol) and heat to 150° C. After 12 hours, heat to 170° C. After 8 hours, cool the reaction mixture and partition between dichloromethane (150 mL) and water. Separate the layers and extract the organic layer with water. Dry the organic layer over Na2SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate/hexane 1/1 to give (1-(2-ethoxyethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonyl-piperidin-4-yl)amine: Rf=0.15 (silica gel, ethyl acetate/hexane).

後処理

  1. waitAfter 8 hours
  2. temperaturecool the reaction mixture
  3. custompartition between dichloromethane (150 mL) and water
  4. customSeparate the layers
  5. extractionextract the organic layer with water
  6. dry with materialDry the organic layer over Na2SO4
  7. filtrationfilter
  8. customevaporate in vacuo
  9. customto give a residue

出典と根拠

ORDレコード
ord-f5b1e0492c1340f09d2a6f9c5b78700a
出典データセット
uspto-grants-2001_04
特許番号
US06211199B1

関連ノート

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