Water → 1-Acetyl-3-[[3-methoxy-4-(trifluoromethyl)phenyl]methylene]piperazine-2,5-dione

HRID 1375019노트

반응식

HRID 1375019 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[CH:6]=O.[C:15]([N:18]1[CH2:23][C:22](=[O:24])[N:21](C(=O)C)[CH2:20][C:19]1=[O:28])(=[O:17])[CH3:16].CC(C)([O-])C.[K+].O>CN(C)C=O.C(O)(C)(C)C.C(OCC)(=O)C>[C:15]([N:18]1[CH2:23][C:22](=[O:24])[NH:21][C:20](=[CH:6][C:5]2[CH:8]=[CH:9][C:10]([C:11]([F:14])([F:13])[F:12])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:19]1=[O:28])(=[O:17])[CH3:16]

참가 물질

8

반응물 4

HCID 962WaterHCID 5403711,4-Diacetyl-2,5-piperazinedioneHCID 179641703-Methoxy-4-(trifluoromethyl)benzaldehydeHCID 23665647Potassium tert-butoxide

생성물 1

HCID 694200991-Acetyl-3-[[3-methoxy-4-(trifluoromethyl)phenyl]methylene]piperazine-2,5-dione

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 6386tert-Butanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred mixture of crude 3-methoxy-4-(trifluoromethyl)-benzaldehyde and 1,4-diacetylpiperazine-2,5-dione (1.98 g) in a mixture of N,N-dimethylformamide (10 ml) and tert-butanol (10 ml) was added potassium tert-butoxide (1.12 g) at 5° C. The mixture was stirred for 18 hours at room temperature. Water (30 ml) and ethyl acetate (100 ml) were added to the mixture and the organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined extract was washed with water, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with 50% of ethyl acetate in hexane as an eluent to give 1-acetyl-3-[[3-methoxy-4-(trifluoromethyl)phenyl]methylene]piperazine-2,5-dione (2.11 g) as a powder.

후처리

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. extractionThe combined extract
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography on silica gel with 50% of ethyl acetate in hexane as an eluent

출처 및 근거

ORD 기록
ord-f49e23d9496549a4970675962c087491
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07166598B2

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