Trifluoroacetic acid → 1-(3,4-Dichlorobenzyl)piperazine

HRID 430675Notes

Reaction equation

HRID 430675 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=2)[CH2:17][CH2:16]1)=O)(C)(C)C.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:29][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][C:25]=1[Cl:28])[CH2:21][N:18]1[CH2:19][CH2:20][NH:15][CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 222577251-(Tert-butoxycarbonyl)-4-(3,4-dichlorobenzyl)piperazine

Product 1

HCID 27580741-(3,4-Dichlorobenzyl)piperazineYield 112.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Trifluoroacetic acid (75 ml, 974 mmol) was added to a solution 1-(tert-butoxycarbonyl)-4-(3,4-dichlorobenzyl)piperazine (45 g, 130 mmol) in chloroform (75 ml). The reaction mixture was stirred for 1 h at room temperature and then made basic with a sodium hydroxide solution. The product was extracted into ethyl acetate and the organic layer was washed with sodium bicarbonate solution, dried over magnesium sulfate and concentrated in vacuo to give 1-(3,4-dichlorobenzyl)piperazine (35.8 g) as a solid.

Workup

  1. extractionThe product was extracted into ethyl acetate
  2. washthe organic layer was washed with sodium bicarbonate solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b22c2c289f464361add26c32d9917d85
Source dataset
uspto-grants-2001_11
Patent number
US06323223B1

Reaction notes

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