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

HRID 1375019ノート

反応式

HRID 1375019 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f49e23d9496549a4970675962c087491
出典データセット
uspto-grants-2007_01
特許番号
US07166598B2

反応ノート

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