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3H-spiro(isobenzofuran-1,4'-piperidin)-3-one → HCID 46213795, 화합물

HRID 1182735
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인쇄 미리보기

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HRID 1182735 반응식
Br[C:2]1[N:11]2[C:5]([CH2:6][N:7]([CH3:17])[CH2:8][C:9]3[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:10]=32)=[N:4][N:3]=1.[NH:18]1[CH2:23][CH2:22][C:21]2([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[C:25](=[O:32])[O:24]2)[CH2:20][CH2:19]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.S1(CCCC1)(=O)=O>[Cl:16][C:14]1[CH:13]=[CH:12][C:10]2[N:11]3[C:2]([N:18]4[CH2:23][CH2:22][C:21]5([C:27]6[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=6[C:25](=[O:32])[O:24]5)[CH2:20][CH2:19]4)=[N:3][N:4]=[C:5]3[CH2:6][N:7]([CH3:17])[CH2:8][C:9]=2[CH:15]=1
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참가 물질

5

반응물 2

HCID 98342553H-spiro(isobenzofuran-1,4'-piperidin)-3-oneHCID 68629339HCID 68629339, 화합물

생성물 1

HCID 46213795HCID 46213795, 화합물수율 14.3%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 31347Sulfolane용매

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온도
160 °C

실험 절차

A mixture of 1-bromo-8-chloro-5-methyl-5,6-dihydro-4H-2,3,5,10b-tetraaza-benzoazulene (50 mg, 0.16 mmol), tetrabutylammonium bromide (10 mg, 0.031 mmol) and 3H-spiro[2-benzofuran-1,4′-piperidin]-3-one (65 mg, 0.32 mmol) in sulfolane (0.5 ml) was stirred for 20 h at 160° C. The reaction mixture was poured on water and extracted with tert-butyl methyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo. Residual sulfolane was evaporated by kugelrohrdistillation (120° C., 1-2 mbar). Preparative HPLC with n-heptane/2-propanol (70:30) as eluent gave the title compound (10 mg, 14%) as light yellow solid. MS m/e: 436 (M+H+).

후처리

  1. additionThe reaction mixture was poured on water
  2. extractionextracted with tert-butyl methyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customResidual sulfolane was evaporated by kugelrohrdistillation (120° C., 1-2 mbar)

출처 및 근거

ORD 기록
ord-e5b1570fe7a04413a4073bd9d7db841f
출처 데이터셋
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08664216B2

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