Chloroacetyl chloride → HCID 58529757, compound

HRID 1972720Notes

Reaction equation

HRID 1972720 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.C([O-])(=O)C.[Na+].[Cl:21][CH2:22][C:23](Cl)=[O:24]>CC(C)=O.O.CCOC(C)=O>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:23](=[O:24])[CH2:22][Cl:21])[CH:10]([CH2:14][OH:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 517045Sodium AcetateHCID 2756656(4-benzylpiperazin-2-yl)methanol

Product 1

HCID 58529757HCID 58529757, compoundYield 99.4%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of (4-benzyl-piperazin-2-yl)methanol (500 mg, 2.42 mmol) and sodium acetate (397.6 mg, 4.85 mmol, 2.0 eq) in acetone (9.7 mL) and water (24.2 mL) under N2 at 0° C. was added dropwise chloroacetyl chloride (0.20 mL, 2.54 mmol, 1.05 eq) over 5 minutes. The mixture was stirred at 0° C. for 5 min and at rt for 1 h. The mixture was diluted with EtOAc (150 mL) and the organic phase was washed with water, aqueous saturated NaHCO3 solution, and brine. The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo to give 680 mg (99%) of the desired product as an oil. 1H-NMR (300 MHz, CD3OD) δ 7.32 to 7.23 (m, 5H), 4.51 (d, 1H), 4.32 to 3.98 (m, 4H), 3.82 to 3.73 (m, 1H), 3.62 to 3.42 (m, 3H), 3.06 to 3.00 (m, 1H), 2.91 to 2.82 (m, 2H), 2.25 to 1.98 (m, 2H).

Workup

  1. washthe organic phase was washed with water, aqueous saturated NaHCO3 solution, and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0de54f41533642d882564cbc61b7b482
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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