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

HRID 323183

반응식

HRID 323183 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 21226206Ethyl acetate hexane용매

반응 조건

온도
170 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f5b1e0492c1340f09d2a6f9c5b78700a
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211199B1

연결된 노트

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