Piperidine → (E)-1-(3-hydroxypropyl)-4-(2-(9-(2-(2-methoxyethoxy)ethyl)-9H-carbazol-3-yl)vinyl)-quinolinium bromide

HRID 1774079노트

반응식

HRID 1774079 반응식
[Br-:1].[OH:2][CH2:3][CH2:4][CH2:5][N+:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH3:16])=[CH:8][CH:7]=1.[CH3:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][N:24]1[C:36]2[CH:35]=[CH:34][C:33]([CH:37]=O)=[CH:32][C:31]=2[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2.N1CCCCC1>C(O)C>[Br-:1].[OH:2][CH2:3][CH2:4][CH2:5][N+:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](/[CH:16]=[CH:37]/[C:33]2[CH:34]=[CH:35][C:36]3[N:24]([CH2:23][CH2:22][O:21][CH2:20][CH2:19][O:18][CH3:17])[C:25]4[C:30]([C:31]=3[CH:32]=2)=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:8][CH:7]=1

참가 물질

5

반응물 3

HCID 8082PiperidineHCID 223147091-(3-Hydroxypropyl)-4-methylquinolinium bromideHCID 866726799-(2-(2-methoxyethoxy)ethyl)-9H-carbazole-3-carbaldehyde

생성물 1

HCID 66575885(E)-1-(3-hydroxypropyl)-4-(2-(9-(2-(2-methoxyethoxy)ethyl)-9H-carbazol-3-yl)vinyl)-quinolinium bromide수율 41%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution mixture of 7 (0.17 g, 0.6 mmol), 3a (0.24 g, 0.8 mmol) and piperidine (0.1 mL) in ethanol (40 mL) was heated to reflux overnight. After cooling down to room temperature, the organic solvent was removed. The residue was purified by precipitation from methanol and ethyl acetate to afford SLOH-Pr (0.14 g) in 41% yield.1H NMR (400 MHz, DMSO-d6) δ 9.29 (d, J=6.8 Hz, 1H), 9.15 (d, J=8.4 Hz, 1H), 8.88 (s, 1H), 8.51 (d, J=6.8 Hz, 1H), 8.45 (d, J=16 Hz, 1H), 8.37 (d, J=16 Hz, 1H), 8.28-8.24 (m, 2H), 8.13 (d, J=8.4 Hz, 1H), 8.05 (t, J=8.0 Hz, 1H), 7.77 (d, J=8.8 Hz, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.52 (t, J=7.6 Hz, 1H), 7.31 (t, J=7.2 Hz, 1H), 5.01 (t, J=7.2 Hz, 2H), 4.86 (t, J=5.2 Hz, 1H), 4.63 (t, J=4.8 Hz, 2H), 3.84 (t, J=5.2 Hz, 2H), 3.55 (tr, J=5.2 Hz, 2H), 3.47 (t, J=5.6 Hz, 2H), 3.31 (t, J=4.8 Hz, 2H), 3.11 (s, 3H), 2.13 (t, J=6.0 Hz, 2H). 13C NMR (400 MHz, DMSO-d6) δ 153.3, 147.3, 145.1, 142.2, 140.9, 137.9, 135.0, 128.8, 127.4, 126.8, 126.7, 126.5, 126.4, 122.8, 122.2, 121.8, 120.4, 119.9, 119.0, 116.3, 115.2, 110.5, 110.4, 71.3, 69.8, 68.9, 58.1, 57.6, 54.2, 42.9, 32.0. HRMS (MALDI-TOF) m/z Calcd for C31H33N2O3 481.2485 Found 481.2458 [M]+.

후처리

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customthe organic solvent was removed
  4. customThe residue was purified by precipitation from methanol and ethyl acetate
  5. customto afford SLOH-Pr (0.14 g) in 41% yield

출처 및 근거

ORD 기록
ord-01236decfe5c438e80b42d4f2772f0aa
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255933B2

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