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Triethylamine → 6-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One

HRID 897202
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HRID 897202 반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[Br:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[O:31][C:30](=[O:35])[CH:29]=[C:28]2OS(C(F)(F)F)(=O)=O>C(#N)C>[Br:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][CH:34]=1)[O:31][C:30](=[O:35])[CH:29]=[C:28]2[NH:1][CH:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH:9]=[CH:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:4][CH2:3]1
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 544281014-Amino-1-cinnamylpiperidineHCID 601491964-[[(Trifluoromethyl)sulfonyl]oxy]-6-bromocoumarin

생성물 1

HCID 737123526-Bromo-4-[1-(3-phenyl-allyl)-piperidine-4-ylamino]-chromen-2-One수율 34.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
150 °C

실험 절차

To a solution of 4-amino-1-cinnamylpiperidine (1.3 g, 6 mmol) and triethylamine (1.6 mL, 7.2 mmol) in dry acetonitrile (125 mL) was added trifluoromethanesulfonic acid 6-bromo-2-oxo-2H-chromen-4-yl ester (2.23 g, 6 mmol). About 5 mL of solution was added to each of 25 dry microwave vials equipped with stir bars. The vials were capped and each was heated at 150° C. for 5 minutes in the microwave. The solutions were combined, concentrated and dissolved in chloroform. The solution was washed with water and brine and dried over Na2SO4, and concentrated. The residue was purified by flash chromatography through a silica gel column with dichloromethane and methanol (95:5 v/v) to provide the desired compound (900 mg, 34%) as a yellow solid. MS (ESI(+)Q1MS m/z 440 (M+2H)+; 1H NMR (300 MHz, DMSO) δ ppm 1.57-1.67 (m, 2H), 1.89-1.95 (m, 2H), 2.13 (m, 2H), 2.92 (m, 2H), 3.13 (m, 2H), 3.50 (m, 1H), 5.28 (sd, 1H), 6.35 (dt, 1H), 6.56 (d, 1H), 7.24-7.47 (m. 7H), 7.74 (dd, 1H), 8.45 (d, 1H).

후처리

  1. customdry microwave vials
  2. customequipped with stir bars
  3. customThe vials were capped
  4. concentrationconcentrated
  5. dissolutiondissolved in chloroform
  6. washThe solution was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography through a silica gel column with dichloromethane and methanol (95:5 v/v)

출처 및 근거

ORD 기록
ord-cdabeadd1bfa4657ad47c2403af8ae7b
출처 데이터셋
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06921821B2

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