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Potassium Carbonate → {1-[2-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-2-hydroxy-ethyl]-piperidin-4-yl}-(4-methoxy-benzothiazol-2-yl)-methanone

HRID 1012945
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HRID 1012945 반응식
[CH3:1][O:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)=[O:13])[S:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[O:20]1[CH2:22][CH:21]1[C:23]1[CH:32]=[CH:31][C:26]2[O:27][CH2:28][CH2:29][O:30][C:25]=2[CH:24]=1.Cl([O-])(=O)(=O)=O.[Li+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[O:27]1[C:26]2[CH:31]=[CH:32][C:23]([CH:21]([OH:20])[CH2:22][N:17]3[CH2:18][CH2:19][CH:14]([C:12]([C:10]4[S:11][C:7]5[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:8]=5[N:9]=4)=[O:13])[CH2:15][CH2:16]3)=[CH:24][C:25]=2[O:30][CH2:29][CH2:28]1
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 167813336-(Oxiran-2-yl)-2,3-dihydro-1,4-benzodioxineHCID 23665649Lithium perchlorateHCID 67315952(4-Methoxy-benzothiazol-2-yl)-piperidin-4-yl-methanone

생성물 1

HCID 67316803{1-[2-(2,3-Dihydro-benzo[1,4]dioxin-6-yl)-2-hydroxy-ethyl]-piperidin-4-yl}-(4-methoxy-benzothiazol-2-yl)-methanone수율 73.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

A mixture of (4-methoxy-benzothiazol-2-yl)-piperidin-4-yl-methanone (83 mg, 0.3 mmol), 6-oxiranyl-2,3-dihydro-benzo[1,4]dioxine (53.5 mg, 0.3 mmol), lithium perchlorate (32 mg, 0.3 mmol) and potassium carbonate (42 mg, 0.3 mmol) in DMF (2 ml) was heated at 80° C. overnight. The mixture was poured on water and extracted with EtOAc. Organic extracts were washed with water and brine, dried over MgSO4 and concentrated. Chromatography on SiO2 (EtOAc/MeOH 9:1) gave the title compound as a beige solid (100 mg, 73%, 4:1 mixture of regioisomers).

후처리

  1. additionThe mixture was poured on water
  2. extractionextracted with EtOAc
  3. washOrganic extracts were washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-72d078c67fda4036aedb62b9acd30b08
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07981886B2

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