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

HRID 1477340Notes

Reaction equation

HRID 1477340 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][N:8]1[C:20]2[CH:19]=[CH:18][C:17]([CH:21]=O)=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2.[I-:23].[CH3:24][N+:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:28]([CH3:35])=[CH:27][CH:26]=1.N1CCCCC1>C(O)C>[I-:23].[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][N:8]1[C:20]2[CH:19]=[CH:18][C:17](/[CH:21]=[CH:35]/[C:28]3[C:29]4[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=4)[N+:25]([CH3:24])=[CH:26][CH:27]=3)=[CH:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2

Participants

5

Reactant 3

HCID 8082PiperidineHCID 110769741,4-Dimethylquinolinium iodideHCID 866726799-(2-(2-methoxyethoxy)ethyl)-9H-carbazole-3-carbaldehyde

Product 1

HCID 57326945(E)-4-(2-(9-(2-(2-methoxyethoxy)ethyl)-9H-carbazol-3-yl)vinyl)-1-methylquinolinium iodideYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution mixture of 3a (0.14 g, 0.5 mmol), 4 (0.18 g, 0.6 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 recrystallization from methanol to afford SLM (0.24 g) as red solid in 56% yield. 1H NMR (400 MHz, DMSO-d6) δ 9.28 (d, J=6.4 Hz, 1H), 9.14 (d, J=8.4 Hz, 1H), 8.86 (s, 1H), 8.51 (d, J=6.4 Hz, 1H), 8.42 (m, 3H), 8.28 (m, 2H), 8.13 (d, J=8.8 Hz, 1H), 8.08 (t, J=7.2 Hz, 1H), 7.80 (d, J=8.8 Hz, 1H), 7.71 (d, J=8.0 Hz, 1H), 7.53 (t, J=8.0 Hz, 1H), 7.32 (t, J=7.2 Hz, 1H), 4.64 (t, J=5.2 Hz, 2H), 4.52 (s, 3H), 3.84 (t, J=5.2 Hz, 2H), 3.48 (m, 2H), 3.33 (m, 2H), 3.11 (s, 3H). 13C NMR (400 MHz, DMSO-d6) δ 153.0, 147, 144.9, 142.1, 140.9, 138.8, 134.9, 129.0, 127.3, 126.7, 126.4, 126.1, 122.8, 122.2, 121.7, 120.4, 119.9, 119.3, 116.2, 115.1, 110.5, 110.4, 71.3, 69.8, 68.9, 58.1, 44.2, 42.9. HRMS (MALDI-TOF) m/z Calcd for C29H29N2O2 437.2223. Found 437.2207 [M+].

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customthe organic solvent was removed
  4. customThe residue was purified by recrystallization from methanol
  5. customto afford SLM (0.24 g) as red solid in 56% yield

Sources & evidence

ORD record
ord-091de7a1175241b78fbcdde5d98a0b36
Source dataset
uspto-grants-2016_08
Patent number
US09403794B2

Reaction notes

Loading…