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

HRID 1477343Notes

Reaction equation

HRID 1477343 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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]+.

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 SLOH-Pr (0.14 g) in 41% yield

Sources & evidence

ORD record
ord-b13cd0acb385453ba97c19acc92a2944
Source dataset
uspto-grants-2016_08
Patent number
US09403794B2

Reaction notes

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