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Piperidine → 2-[4-(3-Piperidin-1-yl-propoxy)-phenyl]-imidazo[1,2-a]pyridine

HRID 1072049
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HRID 1072049 반응식
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:13]=[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][N:15]3[CH:20]=2)=[CH:8][CH:7]=1.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>>[N:21]1([CH2:2][CH2:3][CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3[N:13]=[C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][N:15]4[CH:20]=3)=[CH:8][CH:7]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

3

반응물 2

HCID 8082PiperidineHCID 140970942-[4-(3-Chloro-propoxy)-phenyl]-imidazo[1,2-a]pyridine

생성물 1

HCID 102686352-[4-(3-Piperidin-1-yl-propoxy)-phenyl]-imidazo[1,2-a]pyridine

실험 절차

The product of Example 16 Step A (60 mg) and piperidine (1.0 mL) were heated at 100° C. for 1.5 hours. The reaction was cooled to ambient temperature and partitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL). The aqueous portion was extracted with a fresh portion of ethyl acetate (10 mL) and the organic portions combined and washed with brine (10 mL). The organic portions were dried over magnesium sulfate, filtered and evaporated. The residue was purified via silica gel chromatography (dichloromethane/methanol) to give the title compound (60 mg). 1H-NMR (CD3OD) δ8.30 (m, 1H), 8.00 (s, 1H), 7.74 (m, 2H), 7.43 (m, 1H), 7.20 (m, 1H), 6.90 (m, 2H), 6.80 (m, 1H), 3.98 (t, J=6.0 Hz, 2H), 2.47 (m, 6H), 1.93 (m, 2H), 1.55 (m, 4H), 1.41 (m, 2H)

후처리

  • custompartitioned between ethyl acetate (10 mL) and saturated sodium bicarbonate solution (10 mL)
  • extractionThe aqueous portion was extracted with a fresh portion of ethyl acetate (10 mL)
  • washwashed with brine (10 mL)
  • dry with materialThe organic portions were dried over magnesium sulfate
  • filtrationfiltered
  • customevaporated
  • customThe residue was purified via silica gel chromatography (dichloromethane/methanol)
  • 출처 및 근거

    ORD 기록
    ord-a3f23900e4684f7ca738fe7cf7da8ad8
    출처 데이터셋
    uspto-grants-2005_06
    DOI
    10.6084/m9.figshare.5104873.v1
    특허 번호
    US06908929B2

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