Benzoyl chloride → 1-Benzoylpiperazine

HRID 992356Notes

Reaction equation

HRID 992356 reaction equation
C(OC([CH:6]1[CH2:11][NH:10][CH2:9][CH2:8][NH:7]1)=O)C.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:12]([N:7]1[CH2:6][CH2:11][NH:10][CH2:9][CH2:8]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 10633257Ethyl Piperazine-2-carboxylate

Product 1

HCID 7626541-Benzoylpiperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-ethoxycarbonylpiperazine (4.6 g, 29.1 mmol) in dry methylene chloride (200 mL), was added benzoyl chloride (3.55 ml, 29.1 mmol) and triethylamine (2 ml) sequentially. After stirring for 8 hours at room temperature, a saturated NaHCO3 solution was added and the aqueous phase was extracted with ethyl acetate (3×200 ml). The organic layers were combined, dried over MgSO4 and concentrated to give a crude mixture, which included the desired product XXXIX. The crude was then used for the further reaction without purification.

Workup

  1. extractionthe aqueous phase was extracted with ethyl acetate (3×200 ml)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cd0784794bc5439c984d87fb87adfc12
Source dataset
uspto-grants-2002_10
Patent number
US06469006B1

Reaction notes

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