Water → 1-(2-furanylmethyl)-N-(4-piperidinyl)-1H-benzimidazol-2-amine

HRID 323479노트

반응식

HRID 323479 반응식
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH:16][CH:17]1[CH2:22][CH2:21][N:20](C(OCC)=O)[CH2:19][CH2:18]1.[OH-].[K+].O.NN.O>C(O)CO.ClCCl.CO.CO.C(OCC)(=O)C.C(OCC)(=O)C>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]=[C:8]1[NH:16][CH:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]1

참가 물질

10

반응물 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 13587981(1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine

생성물 1

HCID 135879951-(2-furanylmethyl)-N-(4-piperidinyl)-1H-benzimidazol-2-amine

시약·촉매·용매 5

HCID 174Ethylene Glycol용매HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매HCID 21584119Ethylacetate methanol용매3회

실험 절차

Combine (1-(fur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine (1.38 g, 3.75 mmol), potassium hydroxide (3.0 g, 56.1 mmol) in ethylene glycol (15 mL). Add hydrazine hydrate (3.09 mL, 63.7 mmol). Heat to reflux. After 18 hours, cool, add water, and extract four times with dichloromethane (200 mL). Combine the organic layers, dry over MgSO4, filter, and concentrate in vacuo to obtain a residue. Chromatograph the residue on silica gel eluting with sequentially with ethyl acetate, 25% methanol/ethyl acetate, 50% methanol/ethyl acetate, 75% methanol/ethyl acetate, and then methanol to give a residue. Dissolve the residue in dichloromethane, extract with water and then brine, dry over MgSO4, filter, and evaporate in vacuo to give the title compound.

후처리

  1. temperatureHeat to reflux
  2. temperaturecool
  3. extractionextract four times with dichloromethane (200 mL)
  4. dry with materialCombine the organic layers, dry over MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customto obtain a residue
  8. extractionextract with water
  9. dry with materialbrine, dry over MgSO4
  10. filtrationfilter
  11. customevaporate in vacuo

출처 및 근거

ORD 기록
ord-9141a55894aa4b809a238c8def6b840c
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211199B1

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