Tetrahydrofuran → (1-(5-hydroxymethylfur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine

HRID 323339

반응식

HRID 323339 반응식
C([O:3][C:4]([C:6]1[O:10][C:9]([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23]2)=[CH:8][CH:7]=1)=O)C.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CC(C)=O.ClCCl>ClCCl>[OH:3][CH2:4][C:6]1[O:10][C:9]([CH2:11][N:12]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[NH:21][CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23]2)=[CH:8][CH:7]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 21584124Propan-2-one--dichloromethane (1/1)HCID 22009363(1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine

생성물 1

HCID 22009043(1-(5-hydroxymethylfur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Combine (1-(5-(ethoxycarbonyl)fur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine (1.0 g, 2.27 mmol) and tetrahydrofuran (10 mL). Add dropwise a solution of lithium aluminum hydride (2.3 mL, 1 M in THF, 2.3 mmol). After 5.5 hours, dilute the reaction mixture with dichloromethane and quench by slow portionwise addition of Glauber's salt (Na2SO4.10 H2O) until gas evolution ceases. Add dichloromethane and celite and stir. Filter, rinse the solids with dichloromethane, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 40% acetone/dichloromethane to give a residue. Recrystallization from ethyl acetate/hexane to give (1-(5-hydroxymethylfur-2-ylmethyl)-1H-benzimidazol-2-yl)(1-ethoxycarbonylpiperidin-4-yl)amine: mp; 138-140° C. Elemental Analysis calculated for C21H26N4O4: C 63,30; H 6.58; N 14.06; Found: C 63.29; H 6.50; N 14.06.

후처리

  1. customquench by slow portionwise addition of Glauber's salt (Na2SO4.10 H2O) until gas evolution ceases
  2. filtrationFilter
  3. washrinse the solids with dichloromethane
  4. customevaporate in vacuo
  5. customto give a residue
  6. customRecrystallization from ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-55f57fe017194a9cafdffa6dc6ed98ae
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211199B1

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