Phenylacetic Acid → 2,5-Dimethyl-1-(phenylacetyl)-piperazine

HRID 38272

Reaction equation

HRID 38272 reaction equation
C(N(C(C)C)CC)(C)C.[CH3:10][C@H:11]1[CH2:16][NH:15][C@H:14]([CH3:17])[CH2:13][NH:12]1.[C:18]1([CH2:24][C:25](O)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[CH3:10][CH:11]1[CH2:16][NH:15][CH:14]([CH3:17])[CH2:13][N:12]1[C:25](=[O:26])[CH2:24][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 999Phenylacetic AcidHCID 81531DiisopropylethylamineHCID 2206722,5-Dimethylpiperazine, trans-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 649793942,5-Dimethyl-1-(phenylacetyl)-piperazineYield 178.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Diisopropylethylamine (0.38 ml) was added to a solution of trans-2,5-dimethyl-piperazine (1.50 g), phenyl acetic acid (0.59 g) and HATU (1.55 g) in DMF (10 ml). The reaction mixture was stirred overnight at ambient temperature. The solution was diluted with water, then extracted with ethyl acetate. The organic extracts were dried (MgSO4) then concentrated in vacuo to give the sub-title compound (1.8 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic extracts were dried (MgSO4)
  3. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-715e1f13ccc9473e8841e52835088166
Source dataset
uspto-grants-2013_09
Patent number
US08524715B2

Linked notes

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