5-Bromothiophene-2-carbaldehyde → Tert-butyl 4-(5-formylthiophen-2-yl)piperazine-1-carboxylate

HRID 16745

反応式

HRID 16745 の反応式
Br[C:2]1[S:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.[N:9]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(N(C(C)C)C(C)C)C>CS(C)=O>[CH:7]([C:5]1[S:6][C:2]([N:12]2[CH2:11][CH2:10][N:9]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13]2)=[CH:3][CH:4]=1)=[O:8]

参加物

5

反応物 3

HCID 784285-Bromothiophene-2-carbaldehydeHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

生成物 1

HCID 28065298Tert-butyl 4-(5-formylthiophen-2-yl)piperazine-1-carboxylate収率 73%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
130 °C

実験手順

A mixture of 5-bromothiophene-2-carboxaldehyde (3.82 g, 20.0 mmol), tert-butyl piperazine-1-carboxylate (4.1 g, 22.0 mmol), N-ethyl-N,N-diisopropylamine (7.0 ml, 40.0 mmol) and dimethylsulphoxide (5.0 ml) were stirred at 130° C. under an atmosphere of nitrogen for 18 h. The cooled mixture was partitioned between ethyl acetate and water. The organics were washed with water, brine, dried over magnesium sulphate and evaporated. The resultant dark red solid was purified by silica column chromatography, eluting with dichloromethane followed by ethyl acetate/dichloromethane (15%) to give tert-butyl 4-(5-formylthien-2-yl)piperazine-1-carboxylate (4.3 g, 73%).

後処理

  1. customThe cooled mixture was partitioned between ethyl acetate and water
  2. washThe organics were washed with water, brine
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe resultant dark red solid was purified by silica column chromatography
  6. washeluting with dichloromethane

出典と根拠

ORDレコード
ord-c417a6ea2d5f4f54842f9fa9a25eed89
出典データセット
uspto-grants-2010_06
特許番号
US07737149B2

関連ノート

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