Sodium Hydroxide → 5-Fluoro-3-piperazino benzofuran

HRID 2241973Notes

Reaction equation

HRID 2241973 reaction equation
C(OC([N:6]1[CH2:11][CH2:10][N:9]([C:12]2[C:16]3[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]=3[O:14][CH:13]=2)[CH2:8][CH2:7]1)=O)C.[OH-].[Na+]>C(O)C>[F:21][C:18]1[CH:19]=[CH:20][C:15]2[O:14][CH:13]=[C:12]([N:9]3[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]3)[C:16]=2[CH:17]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 592048394-(5-Fluorobenzofuran-3-yl)-piperazine-1-carboxylic acid ethyl ester

Product 1

HCID 214718555-Fluoro-3-piperazino benzofuranYield 35.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(5-fluorobenzofuran-3-yl)-piperazine-1-carboxylic acid ethyl ester (Step 1, 3 g) was dissolved in 95% ethanol and 3N aqueous sodium hydroxide (25 mL) was added. The reaction mixture was stirred at reflux for 24 hours. The mixture was then cooled to room temperature, concentrated on a rotary evaporator to remove the ethanol and extracted with chloroform. The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered and concentrated on a rotary evaporator. The desired product (0.8 g) was obtained as a brown oil and was used without further purification; MS (ES) m/z (relative intensity): 221 (M+H)+ (100).

Workup

  1. temperatureat reflux for 24 hours
  2. concentrationconcentrated on a rotary evaporator
  3. customto remove the ethanol
  4. extractionextracted with chloroform
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-ba9a9fff95924b1099635ac2aea0ca82
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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