Trifluoroacetic acid → 3,3-Diphenyl-1-(piperazin-1-yl)propan-1-one

HRID 456427Notes

Reaction equation

HRID 456427 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:29])[CH2:15][CH:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:23]1([CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:29])[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 16617197Tert-butyl 4-(3,3-diphenylpropanoyl)piperazine-1-carboxylate

Product 1

HCID 30301473,3-Diphenyl-1-(piperazin-1-yl)propan-1-oneYield 102.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3,3-diphenyl-propionyl)-piperazine-1-carboxylic acid tert-butyl ester (2.15 g, 5.45 mmol) in dry CH2Cl2 (60 ml) was added TFA (20 ml) and resulting mixture stirred at room temperature for 3 hrs. Solvent and excess TFA was then evaporated and the residue was dissolved in CH2Cl2 (150 ml) and washed with sat. NaHCO3 (2×) and dried over MgSO4. Evaporation of solvent gave 1.65 g of pure product.

Workup

  1. customresulting mixture
  2. customSolvent and excess TFA was then evaporated
  3. dissolutionthe residue was dissolved in CH2Cl2 (150 ml)
  4. washwashed with sat. NaHCO3 (2×)
  5. dry with materialdried over MgSO4
  6. customEvaporation of solvent

Sources & evidence

ORD record
ord-ac81fbfef3634a84aee8bf82cab8d2c9
Source dataset
uspto-grants-2007_03
Patent number
US07186726B2

Reaction notes

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