Ethyl Acetate → HCID 13587984、化合物

HRID 323486ノート

反応式

HRID 323486 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]1.[H-].[Na+].Cl[CH2:25][C:26]1[CH:30]=[CH:29][O:28][CH:27]=1.C(OCC)(=O)C>O1CCCC1.CN(C)C=O>[O:28]1[CH:29]=[CH:30][C:26]([CH2:25][N:1]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=[C:2]2[NH:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH:27]1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 30184551-Piperidinecarboxylic acid, 4-(1H-benzimidazol-2-ylamino)-, ethyl esterHCID 111262283-(Chloromethyl)furan

生成物 1

HCID 13587984HCID 13587984、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Combine (1H-benzimidazol-2-yl)-(1-ethoxycarbonyl-piperidin-4-yl)amine (1.5 g, 5.2 mmol) in tetrahydrofuran (45 mL) and dimethylformamide (5 mL). Cool in an ice-bath. Add sodium hydride (0.25 g, 60% n in oil, 6.24 mmol). After 3.5 hours, add 3-(chloromethyl)furan (0.91 g, 7.8 mmol). Warm to ambient temperature. After 60 hours, quench by the addition of Glauber's salt (Na2SO4 10 H2O). Evaporate to remove most of the tetrahydrofuran, dilute with ethyl acetate, and extract with a saturated aqueous sodium bicarbonate solution, water, and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with ethyl acetate to give (1-(fur-3-ylmethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine: Rf=0.32 (silica gel, ethyl acetate).

後処理

  1. temperatureCool in an ice-bath
  2. waitAfter 60 hours
  3. customquench by the addition of Glauber's salt (Na2SO4 10 H2O)
  4. customEvaporate
  5. customto remove most of the tetrahydrofuran
  6. additiondilute with ethyl acetate
  7. extractionextract with a saturated aqueous sodium bicarbonate solution, water
  8. dry with materialDry the organic layer over MgSO4
  9. filtrationfilter
  10. customevaporate in vacuo
  11. customto give a residue

出典と根拠

ORDレコード
ord-331412c317be416cadfdbf628ea3d58a
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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