1-Phenylpiperazine → HCID 698982, compound

HRID 2380959Notes

Reaction equation

HRID 2380959 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]1([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.C(OCC)(=O)C>O1CCOCC1>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([N:22]2[CH2:23][CH2:24][N:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:20][CH2:21]2)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 70961-PhenylpiperazineHCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 8857Ethyl Acetate

Product 1

HCID 698982HCID 698982, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a stirred solution of 4-nitrobenzoyl chloride (6.23 g, 33.9 mmol) and N-phenyl piperazine (4.71 ml, 30.8 mmol) in anhydrous dioxane (250 ml) at 0° C. was added triethylamine (4.73 ml, 33.9 mmol) and the mixture was then stirred at reflux (110° C.) for 5 hours. The reaction was allowed to cool then quenched with water (100 ml) and the resulting aqueous mixture was extracted with ethyl acetate (2×75 ml). The organic extracts were combined, dried over magnesium sulfate and concentrated to yield crude product as a yellow oil. Pure product was obtained by crystallisation from a mixture of 40% ethyl acetate in petrol to afford the title compound as a white crystalline solid (6.5 g, 62%). HPLC retention time 6.9 min. Mass spectrum (ES+) m/z 312 (M+H).

Workup

  1. temperatureto cool
  2. customthen quenched with water (100 ml)
  3. extractionthe resulting aqueous mixture was extracted with ethyl acetate (2×75 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto yield crude product as a yellow oil

Sources & evidence

ORD record
ord-7b4fcef7b8c74de380d56990c2aba04a
Source dataset
uspto-grants-2012_09
Patent number
US08258138B2

Reaction notes

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