Triethylamine → 1-[4-(2-Chloro-4-nitrophenyl)piperazin-1-yl]-2-methylpropan-1-one

HRID 38247

Reaction equation

HRID 38247 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].CCN(CC)CC.[Cl:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>C(Cl)Cl>[Cl:14][C:15]1[CH:20]=[C:19]([N+:21]([O-:23])=[O:22])[CH:18]=[CH:17][C:16]=1[N:24]1[CH2:29][CH2:28][N:27]([C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[CH2:26][CH2:25]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 27713311-(2-Chloro-4-nitrophenyl)piperazine

Product 1

HCID 28863371-[4-(2-Chloro-4-nitrophenyl)piperazin-1-yl]-2-methylpropan-1-oneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to Scheme 4 Step 1: Isobutyryl chloride (1.24 mmol, 0.13 mL) and Et3N (2.48 mmol, 0.35 mL) were added to a solution of 1-(2-chloro-4-nitrophenyl)piperazine (0.83 mmol, 200 mg) in DCM (5 mL) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. The organic phase was washed with a saturated solution of NaHCO3. The aqueous phase was extracted with AcOEt. The organic phase was washed with brine, was dried over Na2SO4, was filtered and was concentrated under reduced pressure to afford 1-(4-(2-chloro-4-nitrophenyl)piperazin-1-yl)-2-methylpropan-1-one (0.83 mmol, 261 mg, 100%). The product was used without further purification.

Workup

  1. washThe organic phase was washed with a saturated solution of NaHCO3
  2. extractionThe aqueous phase was extracted with AcOEt
  3. washThe organic phase was washed with brine
  4. dry with materialwas dried over Na2SO4
  5. filtrationwas filtered
  6. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-20b164a09da742bea74ca466d122cbe8
Source dataset
uspto-grants-2013_09
Patent number
US08524726B2

Linked notes

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