Water → Acetic acid 2-[4-(4,6-dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-phenyl ester

HRID 37864Notes

Reaction equation

HRID 37864 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:23]=3[OH:31])[CH2:18][CH2:17]2)[CH:10]=1.[C:32](Cl)(=[O:34])[CH3:33].O>ClCCl>[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[C:11]([N:16]2[CH2:17][CH2:18][N:19]([C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-:30])=[O:29])=[CH:24][C:23]=3[O:31][C:32](=[O:34])[CH3:33])[CH2:20][CH2:21]2)[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 668512292-[4-(4,6-Dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-phenol

Product 1

HCID 66851216Acetic acid 2-[4-(4,6-dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-phenyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.0 mL, 7.17 mmol) was added to a solution of 2-[4-(4,6-dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-phenol (500 mg, 1.52 mmol) in dry dichloromethane (20 mL) followed by the dropwise addition of acetyl chloride (0.2 mL, 2.80 mmol). After stirring for 15 min water was added and the mixture warmed to room temperature. The organic phase was separated and the aqueous phase was extracted with dichloromethane (2×30 mL). The combined organic phases were successively washed with water (2×30 mL) then brine (2×30 mL), dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was triturated with 5% dichloromethane in petroleum ether (2×20 mL) to afford acetic acid 2-[4-(4,6-dimethyl-pyridin-2-yl)-piperazin-1-yl]-5-nitro-phenyl ester (365 mg, 65%) as a pale brownish-yellow solid.

Workup

  1. additionwas added
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted with dichloromethane (2×30 mL)
  4. washThe combined organic phases were successively washed with water (2×30 mL)
  5. dry with materialbrine (2×30 mL), dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with 5% dichloromethane in petroleum ether (2×20 mL)

Sources & evidence

ORD record
ord-e2525fd66f5d46aebb24655d5990b76b
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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