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

HRID 1911317노트

반응식

HRID 1911317 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
130 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-79e16d86aada4d1a8cc4d74715806896
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08604022B2

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