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

HRID 1840732Notes

Reaction equation

HRID 1840732 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-24344936932c4c43ab82bcbc85fa638d
Source dataset
uspto-grants-2004_01
Patent number
US06683074B1

Reaction notes

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