Sodium Hydroxide → (1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine

HRID 323511Notes

Reaction equation

HRID 323511 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[NH:13][CH:14]1[CH2:19][CH2:18][N:17](C(OCC)=O)[CH2:16][CH2:15]1.[OH-].[Na+]>C(O)(C)C.O>[OH:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[NH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22009172(1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine

Product 1

HCID 22009128(1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)(piperidin-4-yl)amine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

Combine (1-(2-hydroxyethyl)-1H-benzimidazol-2-yl)(1-(ethoxycarbonyl)piperidin-4-yl)amine (5.0 mmol) and sodium hydroxide (2.0 g) in isopropanol (20 mL) and water (0.1 mL). Heat to reflux. After 36 hours, cool and evaporate the reaction mixture in vacuo to give a residue. Combine the residue and water. Extract the diluted residue three times with ethyl acetate. Combine the organic layers and extract with brine, dry over Na2SO4, filter, and evaporate in vacuo to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. temperaturecool
  3. customevaporate the reaction mixture in vacuo
  4. customto give a residue
  5. extractionExtract the diluted residue three times with ethyl acetate
  6. extractionextract with brine
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. customevaporate in vacuo

Sources & evidence

ORD record
ord-97b2eacca48f4fa5a7262a1836bb0cc0
Source dataset
uspto-grants-2001_04
Patent number
US06211199B1

Reaction notes

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