Water → HCID 2877281, compound

HRID 2241902Notes

Reaction equation

HRID 2241902 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].C(N(CC)CC)C.[F:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.O>CN(C)C1C=CN=CC=1.O1CCCC1>[F:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[N:23]1[CH2:28][CH2:27][N:26]([C:1](=[O:4])[CH2:2][CH3:3])[CH2:25][CH2:24]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 27830661-(2-fluoro-4-nitrophenyl)piperazine

Product 1

HCID 2877281HCID 2877281, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Propionyl chloride (0.620 g, 4.88 mmol), triethylamine (0.747 ml, 5.32 mmol) and 4-dimethylaminopyridine (0.0542 g, 0.444 mmol) were added to a solution of 1-(2-fluoro-4-nitrophenyl)piperazine (compound of Reference Example 52; 1.00 g, 4.44 mmol) in anhydrous tetrahydrofuran (9 ml) under ice cooling, and the mixture was stirred at room temperature for 6 hours. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The residue obtained by evaporation of the solvent under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1) to give the title compound (0.662 g, 53%) as a yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained by evaporation of the solvent under reduced pressure
  5. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-84c30b5044db463da035ec550a33cb8f
Source dataset
uspto-grants-2010_03
Patent number
US07671058B2

Reaction notes

Loading…