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

HRID 1749252Notes

Reaction equation

HRID 1749252 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-98020d9f6a0c4c559ab474b9dd184d68
Source dataset
uspto-grants-2015_10
Patent number
US09156814B2

Reaction notes

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