3-Fluorobenzoic Acid → 4-(3-Fluoro-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1665663

Reaction equation

HRID 1665663 reaction equation
C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.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].[F:45][C:46]1[CH:47]=[C:48]([CH:52]=[CH:53][CH:54]=1)[C:49](O)=[O:50]>CN(C=O)C.O>[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:49](=[O:50])[C:48]2[CH:52]=[CH:53][CH:54]=[C:46]([F:45])[CH:47]=2)[CH2:41][CH2:40]1)=[O:38])([CH3:35])([CH3:33])[CH3:34]

Participants

8

Reactant 5

HCID 99683-Fluorobenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 578758094-(3-Fluoro-benzoyl)-piperazine-1-carboxylic acid tert-butyl esterYield 107.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

HOBt (290 mg, 2.14 mmol), DIEA (461 mg, 3.5 mmol), EDCI.HCl (410 mg, 2.14 mmol) followed by piperazine-1-carboxylic acid tert-butyl ester (398 mg, 2.14 mmol) were added to a stirred solution of 3-fluorobenzoic acid (250 mg, 1.78 mmol) in DMF (3 mL). The reaction mixture was stirred overnight and then diluted with cold water. The product was extracted with ethyl acetate and the organic layer was washed with brine solution, dried over Na2SO4, and concentrated under reduced pressure to afford 590 mg (92%) of 4-(3-fluoro-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester.

Workup

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

Sources & evidence

ORD record
ord-68db923e4e6b4683a2dfaab4c13215a0
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Linked notes

Loading…