Ethanol → [4-(4-Methyl-piperazin-1-yl)-phenyl]-acetic acid

HRID 1487406Notes

Reaction equation

HRID 1487406 reaction equation
[BH4-].[Na+].C([Se][Se]CC1C=CC=CC=1)C1C=CC=CC=1.ClC(Cl)(Cl)C([C:23]1[CH:28]=[CH:27][C:26]([N:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[CH:25][CH:24]=1)O.[OH-:38].[Na+].[CH2:40]([OH:42])[CH3:41]>>[CH3:35][N:32]1[CH2:33][CH2:34][N:29]([C:26]2[CH:27]=[CH:28][C:23]([CH2:41][C:40]([OH:38])=[O:42])=[CH:24][CH:25]=2)[CH2:30][CH2:31]1

Participants

6

Reactant 5

HCID 702EthanolHCID 14798Sodium HydroxideHCID 95955Dibenzyl diselenideHCID 4311764Sodium borohydrideHCID 682771722,2,2-Trichloro-1-(4-(4-methylpiperazine-1-yl)phenyl)ethanol

Product 1

HCID 28807075[4-(4-Methyl-piperazin-1-yl)-phenyl]-acetic acid

Procedure

0.559 g (14.77 mmol) of sodium borohydride is added quickly to 2.294 g (7.35 mmol) of dibenzyl diselenide in 28 ml of ethanol. The reaction mixture is stirred at room temperature for 1 hour. 2.266 g (7 mmol) of 2,2,2-trichloro-1-(4-(4-methylpiperazine-1-yl)phenyl)ethanol and 1.680 g (42.0 mmol) of sodium hydroxide are then added. The reaction mixture is stirred at 35° C. for 24 hours. The solvent is concentrated and the crude product extracted with ethyl acetate after adding a pH 5 aqueous phase. The organic phases are combined, dried on magnesium sulfate and then concentrated to yield 2-(4-(4-methylpiperazine-1-yl)phenyl)acetic acid which is used without additional purification.

Workup

  1. stirringThe reaction mixture is stirred at 35° C. for 24 hours
  2. concentrationThe solvent is concentrated
  3. extractionthe crude product extracted with ethyl acetate
  4. additionafter adding a pH 5 aqueous phase
  5. customdried on magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-666a6db3f3af40309202b23173b0b754
Source dataset
uspto-grants-2016_08
Patent number
US09428510B2

Reaction notes

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