Triethylamine → HCID 2851076, compound

HRID 880491Notes

Reaction equation

HRID 880491 reaction equation
C(N(CC)CC)C.[N+:8]([C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[CH:13][CH:12]=1)([O-:10])=[O:9].[C:23](Cl)(=[O:27])[CH:24]([CH3:26])[CH3:25]>ClCCl>[CH3:25][CH:24]([CH3:26])[C:23]([N:20]1[CH2:21][CH2:22][N:17]([C:14]2[CH:13]=[CH:12][C:11]([N+:8]([O-:10])=[O:9])=[CH:16][CH:15]=2)[CH2:18][CH2:19]1)=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 804471-(4-Nitrophenyl)piperazine

Product 1

HCID 2851076HCID 2851076, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (976 mg, 9.66 mmol) was added to a solution of 1-(4-nitrophenyl)piperazine (1.00 g, 4.83 mmol) in dichloromethane (20 mL) at 0° C. and stirred for 30 min. Isobutyryl chloride (617 mg, 5.79 mmol) was then added and the mixture was warmed to ambient temperature and stirred for 4 h. the reaction mixture was quenched with ice-water and the organic layer separated. The aqueous layer was extracted with dichloromethane (5×5 mL) and the combined organic layers were washed water, saturated sodium bicarbonate solution, brine, dried over anhydrous sodium sulphate and concentrated in vacuo to afford 2-methyl-1-[4-(4-nitrophenyl)piperazin-1-yl]propan-1-one (1.20 g, 90%) as a yellow solid.

Workup

  1. stirringstirred for 4 h. the reaction mixture
  2. customwas quenched with ice-water
  3. customthe organic layer separated
  4. extractionThe aqueous layer was extracted with dichloromethane (5×5 mL)
  5. washthe combined organic layers were washed water, saturated sodium bicarbonate solution, brine
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fb4fa2e640114739aae6f0f154d24b91
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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