Acetic Anhydride → HCID 53708015, compound

HRID 1596213Notes

Reaction equation

HRID 1596213 reaction equation
[C:1]([O:9][C:10]([N:12]1[CH2:17][CH2:16][NH:15][CH:14]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13]1)=[O:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:30](OC(=O)C)(=[O:32])[CH3:31]>ClCCl.C(Cl)(Cl)Cl>[C:30]([N:15]1[CH2:16][CH2:17][N:12]([C:10]([O:9][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:11])[CH2:13][CH:14]1[C:18]([O:20][CH2:21][CH3:22])=[O:19])(=[O:32])[CH3:31]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 53880449HCID 53880449, compound

Product 1

HCID 53708015HCID 53708015, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of rac-ethyl 4-benzoyloxycarbonylpiperazine-2-carboxylate (4 g) and triethylamine (5.1 ml) in dichloromethane (50 ml) was added acetic anhydride (1.72 ml) at 0° C. The mixture was stirred at ambient temperature for 3 hours, diluted with chloroform and washed with 1N hydrochloric acid, water, saturated aqueous solution of sodium hydrogen carbonate, water, brine, dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography eluting with a mixture of ethyl acetate and n-hexane (2:1) to give rac-ethyl 1-acetyl-4-benzyloxycarbonylpiperazine-2-carboxylate (4.63 g).

Workup

  1. washwashed with 1N hydrochloric acid, water, saturated aqueous solution of sodium hydrogen carbonate, water, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography
  5. washeluting with a mixture of ethyl acetate and n-hexane (2:1)

Sources & evidence

ORD record
ord-14c63bf039dc498c830f99180605b232
Source dataset
uspto-grants-2001_09
Patent number
US06291464B1

Reaction notes

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