Water → HCID 59135577, compound

HRID 2238874Notes

Reaction equation

HRID 2238874 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH:10]([CH2:14][OH:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:24][C:25](Cl)=[O:26]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]2[CH:10]([CH2:14][O:15][CH2:24][C:25]2=[O:26])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 2756656(4-benzylpiperazin-2-yl)methanol

Product 1

HCID 59135577HCID 59135577, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of (4-benzylpiperazin-2-yl)methanol (6.4 g, 30 mmol) prepared according to J. Med. Chem. 1993, 36, 2075-2083, water (100 ml) and tetrahydrofuran (100 ml) were successively added potassium carbonate (8.3 g, 60 mmol) with chloroacetyl chloride (3.6 mL, 45 mmol), and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in ethanol (100 ml), potassium hydroxide (2 g) was added, and the mixture was stirred at 50° C. for 3 hr. The reaction mixture was concentrated under reduced pressure, and the residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (2.6 g, yield 35%) as a yellow oil. MS 247 (M+1).

Workup

  1. customprepared
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. dissolutionThe residue was dissolved in ethanol (100 ml)
  8. additionpotassium hydroxide (2 g) was added
  9. stirringthe mixture was stirred at 50° C. for 3 hr
  10. concentrationThe reaction mixture was concentrated under reduced pressure
  11. customthe residue was partitioned between ethyl acetate and water
  12. washThe organic layer was washed with saturated brine
  13. dry with materialdried over anhydrous magnesium sulfate
  14. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-664590715e564dbd84536ac1b6c71ddf
Source dataset
uspto-grants-2010_05
Patent number
US07718798B2

Reaction notes

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