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

HRID 323479ノート

反応式

HRID 323479 の反応式
[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

参加物

10

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 5

HCID 174Ethylene Glycol溶媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒HCID 21584119Ethylacetate methanol溶媒3 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9141a55894aa4b809a238c8def6b840c
出典データセット
uspto-grants-2001_04
特許番号
US06211199B1

反応ノート

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