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Ethanol → 1-(4-(3-(4-Fluoro-phenyl)cinnamoylamino)benzyl)piperidine

HRID 565919
ノート
印刷プレビュー

反応式

HRID 565919 の反応式
Br[C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=1)[CH:5]=[CH:6][C:7]([NH:9][C:10]1[CH:22]=[CH:21][C:13]([CH2:14][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:12][CH:11]=1)=[O:8].B([O-])([O-])O[C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:34][C:31]1[CH:32]=[CH:33][C:28]([C:2]2[CH:3]=[C:4]([CH:23]=[CH:24][CH:25]=2)[CH:5]=[CH:6][C:7]([NH:9][C:10]2[CH:22]=[CH:21][C:13]([CH2:14][N:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:12][CH:11]=2)=[O:8])=[CH:29][CH:30]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 539077661-(4-(3-Bromocinnamoylamino)benzyl)piperidineHCID 867561584-Fluorophenyl borate

生成物 1

HCID 539677711-(4-(3-(4-Fluoro-phenyl)cinnamoylamino)benzyl)piperidine収率 92.8%

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 1140Toluene溶媒

実験手順

A suspension of 1-(4-(3-bromocinnamoylamino)-benzyl)piperidine (0.4g), 4-fluorophenyl borate (0.14g), 1 M potassium carbonate (2ml) and ethanol (1ml) in toluene (5ml) was stirred under argon atmosphere at room temperature for 30 minutes. To the suspension was added tetrakistriphenylphosphinepalladium (0.05g), and the mixture was refluxed over night. The mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (methanol/triethylamine/ethyl acetate) to give crude crystals, which were recrystallized from ethyl acetate-hexane to give 1-(4-(3-(4-fluoro-phenyl)cinnamoylamino)benzyl)piperidine (Compound 83) (0.35g) as colorless crystals.

後処理

  1. temperaturethe mixture was refluxed over night
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customUnder reduced pressure, the solvent was evaporated
  6. customthe residue was purified with silica gel column (methanol/triethylamine/ethyl acetate)
  7. customto give crude crystals, which
  8. customwere recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-440c896d5886420cb73abd4708602613
出典データセット
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06172061B2

反応ノート

読み込み中…

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