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

HRID 1749252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1749252
[Br-:1].[CH2:2]([N+:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH3:14])=[CH:6][CH:5]=1)[CH3:3].[CH3:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][N:22]1[C:34]2[CH:33]=[CH:32][C:31]([CH:35]=O)=[CH:30][C:29]=2[C:28]2[C:23]1=[CH:24][CH:25]=[CH:26][CH:27]=2.N1CCCCC1>C(O)C>[Br-:1].[CH2:2]([N+:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](/[CH:14]=[CH:35]/[C:31]2[CH:32]=[CH:33][C:34]3[N:22]([CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:16][CH3:15])[C:23]4[C:28]([C:29]=3[CH:30]=2)=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:6][CH:5]=1)[CH3:3]

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 177735061-Ethyl-4-methylquinolinium bromideHCID 866726799-(2-(2-methoxyethoxy)ethyl)-9H-carbazole-3-carbaldehyde

Produkt 1

HCID 66575883(E)-1-ethyl-4-(2-(9-(2-(2-methoxyethoxy)ethyl)-9H-carbazol-3-yl)vinyl)quinolinium bromideAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution mixture of 6 (0.20 g, 0.8 mmol), 3a (0.33 g, 1.1 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 SLE (0.22 g) in 53% yield. 1H NMR (400 MHz, DMSO-d6) δ 9.34 (d, J=8.4 Hz, 1H), 9.15 (d, J=8.4 Hz, 1H), 8.86 (s, 1H), 8.54-8.51 (m, 2H), 8.44 (d, J=16 Hz, 1H), 8.36 (d, J=16 Hz, 1H), 8.28-8.23 (m, 2H), 8.12 (d, J=8.0 Hz, 1H), 8.05 (t, J=7.6 Hz, 1H), 7.77 (d, J=8.4 Hz, 1H), 7.70 (d, J=8.4 Hz, 1H), 7.52 (t, J=7.6 Hz, 1H), 7.31 (t, J=7.6 Hz, 1H), 4.99 (tr, J=6.8 Hz, 2H), 4.63 (t, J=4.8 Hz, 2H), 3.84 (t, J=4.8 Hz, 2H), 3.48 (t, J=4.8 Hz, 2H), 3.31 (t, J=4.8 Hz, 2H), 3.11 (s, 3H), 1.59 (t, J=6.8 Hz, 3H). 13C NMR (400 MHz, DMSO-d6) δ 153.2, 146.7, 145.1, 142.2, 140.9, 137.7, 135.0, 128.9, 127.4, 126.8, 126.7, 126.5, 126.4, 122.8, 122.2, 121.8, 120.4, 119.9, 119.0, 116.2, 115.5, 110.4, 110.3, 71.3, 69.8, 68.9, 58.1, 51.9, 15.1. HRMS (MALDI-TOF) m/z Calcd for C30H31N2O2 451.2380. Found 451.2362 [M]+.

Aufarbeitung

  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 SLE (0.22 g) in 53% yield

Quellen und Nachweise

ORD-Eintrag
ord-98020d9f6a0c4c559ab474b9dd184d68
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156814B2

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