Hydrochloric Acid → HCID 17963978, compound

HRID 1374972Notes

Reaction equation

HRID 1374972 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[CH3:16])[CH:11]=O.[C:17]([N:20]1[CH2:25][C:24](=[O:26])[N:23](C(=O)C)C[C:21]1=[O:30])(=[O:19])[CH3:18].[CH3:31]C(C)([O-])C.[K+].Cl>CN(C)C=O.C(O)(C)(C)C.O>[C:17]([N:20]1[C:25](=[CH2:31])[C:24](=[O:26])[NH:23][CH:11]([C:10]2[CH:13]=[CH:14][C:15]([CH3:16])=[C:8]([O:7][CH2:6][O:5][CH2:4][CH2:3][O:2][CH3:1])[CH:9]=2)[C:21]1=[O:30])(=[O:19])[CH3:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5403711,4-Diacetyl-2,5-piperazinedioneHCID 17964265HCID 17964265, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 17963978HCID 17963978, compoundYield 74.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6386tert-ButanolSolvent

Procedure

To a stirred mixture of 3-[(2-methoxyethoxy)methoxy]-4-methylbenzaldehyde (1.70 g) and 1,4-diacetyl-2,5-piperazinedione (1.6 g) in a mixture of N,N-dimethylformamide (17 ml) and tert-butanol (17 ml) was added potassium tert-butoxide (900 mg) at 5° C. The mixture was stirred for 24 hours at room temperature and then poured into water (300 ml). The aqueous mixture was adjusted to pH 4–5 with aqueous diluted hydrochloric acid solution and extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using mixed solvents of toluene and ethyl acetate (3:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give 1-acetyl-3-[3-[(2-methoxyethoxy)methoxy]-4-methylphenyl]-methylene-2,5-piperazinedione (2.05 g) as a powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated under reduced pressure
  5. customThe resulting residue was purified by column chromatography on silica gel using
  6. additionmixed solvents of toluene and ethyl acetate (3:1)
  7. additionThe fractions containing the objective compound
  8. customwere collected
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-49f88a269b6c4811bc285c187bcf30a5
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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