Piperazin-2-one → HCID 66873515, compound

HRID 249878Notes

Reaction equation

HRID 249878 reaction equation
Cl[C:2]1[O:3][C:4]2[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=2)[N:6]=1.[NH:15]1[CH2:20][CH2:19][NH:18][CH2:17][C:16]1=[O:21]>C1COCC1.CCOC(C)=O.Cl>[O:21]=[C:16]1[NH:15][CH2:20][CH2:19][N:18]([C:2]2[O:3][C:4]3[C:5](=[C:7]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[CH:9][CH:10]=3)[N:6]=2)[CH2:17]1

Participants

6

Reactant 2

HCID 231360Piperazin-2-oneHCID 56924368Methyl 2-chlorobenzo[d]oxazole-4-carboxylate

Product 1

HCID 66873515HCID 66873515, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 2-chlorobenzoxazole-4-carboxylate (750 mg, 3.54 mmol) and piperazin-2-one (780 mg, 7.79 mmol) in THF (60 mL) was stirred at ambient temperature overnight. The reaction mixture was diluted with EtOAc (150 mL) and 1 N HCl (25 ml). The aqueous layer was separated, basified with 1 N NaOH and extracted with EtOAc (6×50 mL). The combined organic extracts were dried (Na2SO4) and concentrated under reduced pressure to give methyl 2-(3-oxopiperazine-1-yl)benzoxazole-4-carboxylate (690 mg, 72%). 1H NMR consistent.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with EtOAc (6×50 mL)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd85b5b02f2b4ddb84b5dc1a65bd8b31
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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