3-Cyanobenzoic acid → Tert-butyl 4-(3-cyanobenzoyl)piperazine-1-carboxylate

HRID 1665665Notes

Reaction equation

HRID 1665665 reaction equation
CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].[C:45]([C:47]1[CH:48]=[C:49]([CH:53]=[CH:54][CH:55]=1)[C:50](O)=[O:51])#[N:46]>CN(C=O)C.O>[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:50](=[O:51])[C:49]2[CH:53]=[CH:54][CH:55]=[C:47]([C:45]#[N:46])[CH:48]=2)[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:33])[CH3:34]

Participants

8

Reactant 5

HCID 158753-Cyanobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 31517243Tert-butyl 4-(3-cyanobenzoyl)piperazine-1-carboxylateYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

DIEA (527 mg, 4.07 mmol), HOBt (322 mg, 2.45 mmol), EDCI.HCl (302 m, 1.5 mmol) and piperazine-1-carboxylic acid tert-butyl ester (456 mg, 2.45 mmol) were added to a stirred solution of 3-cyano-benzoicacid (300 mg, 2.03 mmol) in DMF (3 mL) and the resulting mixture was stirred at ambient temperature overnight. The reaction mixture was then diluted with water and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with brine solution, dried over Na2SO4, and concentrated under reduced pressure to afford 590 mg (92%) of 4-(3-cyano-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b102db29197f4b99ae16ad8f77120b8a
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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