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

HRID 323339Notes

Reaction equation

HRID 323339 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-55f57fe017194a9cafdffa6dc6ed98ae
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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