Trichloroacetic Acid → 2,2,2-Trichloro-1-(4-(4-methylpiperazine-1-yl)phenyl)ethanol

HRID 1487405Notes

Reaction equation

HRID 1487405 reaction equation
[Cl:1][C:2]([Cl:7])([Cl:6])[C:3](O)=[O:4].ClC(Cl)(Cl)C([O-])=O.[Na+].[CH3:16][N:17]1[CH2:22][CH2:21][N:20]([C:23]2[CH:30]=[CH:29][C:26](C=O)=[CH:25][CH:24]=2)[CH2:19][CH2:18]1>CN(C)C=O>[Cl:1][C:2]([Cl:7])([Cl:6])[CH:3]([C:26]1[CH:25]=[CH:24][C:23]([N:20]2[CH2:21][CH2:22][N:17]([CH3:16])[CH2:18][CH2:19]2)=[CH:30][CH:29]=1)[OH:4]

Participants

5

Reactant 3

HCID 6421Trichloroacetic AcidHCID 7365334-(4-Methylpiperazin-1-yl)benzaldehydeHCID 23681045Sodium Trichloroacetate

Product 1

HCID 682771722,2,2-Trichloro-1-(4-(4-methylpiperazine-1-yl)phenyl)ethanolYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 ml (10.00 mmol) of trichloroacetic acid and, in small portions, 1.854 g (10 mmol) of sodium 2,2,2-trichloroacetate are added at room temperature to a solution of 1.362 g (6.67 mmol) of 4-(4-methylpiperazine-1-yl)benzaldehyde in 13.5 ml of dimethylformamide. The reaction mixture is stirred for 3 hours at room temperature. The solvent is concentrated and the crude reaction product extracted with ethyl acetate. The organic phase is washed using saturated sodium bicarbonate solution. The organic phases are combined, dried on magnesium sulfate and then concentrated to yield 1.760 g (yield=82%) of 2,2,2-trichloro-1-(4-(4-methylpiperazine-1-yl)phenyl)ethanol in the form of a white solid.

Workup

  1. concentrationThe solvent is concentrated
  2. customthe crude reaction product
  3. extractionextracted with ethyl acetate
  4. washThe organic phase is washed
  5. customdried on magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b11d578489b443e387a1b3901bf8ed7e
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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