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Dimethylformamide → 4-(3,5,6-Trichloropyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester

HRID 1804119
ノート
印刷プレビュー

反応式

HRID 1804119 の反応式
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[C:4]([Cl:10])[N:3]=1.[C:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O.C1(C)C=CC=CC=1>[C:14]([O:13][C:11]([N:18]1[CH2:23][CH2:22][N:21]([C:2]2[C:7]([Cl:8])=[CH:6][C:5]([Cl:9])=[C:4]([Cl:10])[N:3]=2)[CH2:20][CH2:19]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]
参加物反応条件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 6228DimethylformamideHCID 11430Potassium CarbonateHCID 169902,3,5,6-TetrachloropyridineHCID 143452tert-Butyl piperazine-1-carboxylate

生成物 1

HCID 866587754-(3,5,6-Trichloropyridin-2-yl)piperazine-1-carboxylic acid tert-butyl ester収率 85.6%

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a mixture of 2,3,5,6-tetrachloropyridine (6.51 g), 1-Boc-piperazine (6.71 g) and potassium carbonate (9.95 g) were added dimethylformamide (15 mL) and toluene (30 mL), and the mixture was stirred at 100° C. for 2 hr. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by column chromatography (ethyl acetate:hexane) to give the title compound (9.42 g).

後処理

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by column chromatography (ethyl acetate:hexane)

出典と根拠

ORDレコード
ord-49d385cb3fb24444b4d6d0ba4af67a9a
出典データセット
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08354401B2

反応ノート

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