Piperidine → (E)-1-methyl-4-(2-(9-methyl-9H-carbazol-3-yl)vinyl)quinolinium iodide

HRID 1749254Notes

Reaction equation

HRID 1749254 reaction equation
[I-:1].[CH3:2][N+:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH3:13])=[CH:5][CH:4]=1.[CH3:14][N:15]1[C:27]2[CH:26]=[CH:25][C:24]([CH:28]=O)=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2.N1CCCCC1>C(O)C>[I-:1].[CH3:2][N+:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](/[CH:13]=[CH:28]/[C:24]2[CH:25]=[CH:26][C:27]3[N:15]([CH3:14])[C:16]4[C:21]([C:22]=3[CH:23]=2)=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 6106669-Methyl-9H-carbazole-3-carbaldehydeHCID 110769741,4-Dimethylquinolinium iodide

Product 1

HCID 66575887(E)-1-methyl-4-(2-(9-methyl-9H-carbazol-3-yl)vinyl)quinolinium iodideYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution mixture of 1,4-dimethylquinolinium iodide (0.14 g, 0.5 mmol), 3b (0.13 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 precipitation from methanol and ethyl acetate to afford Me-SLM (0.14 g) in 62% yield. 1H NMR (400 MHz, DMSO-d6) δ 9.27 (d, J=6.4 Hz, 1H), 9.12 (d, J=8.4 Hz, 1H), 8.86 (s, 1H), 8.49 (d, J=6.4 Hz, 1H), 8.45-8.23 (m, 5H), 8.15 (d, J=8.8 Hz, 1H), 8.06 (t, J=7.6 Hz, 1H), 7.75 (d, J=8.4 Hz, 1H), 7.66 (d, J=8.0 Hz, 1H), 7.55 (t, J=7.6 Hz, 1H), 7.32 (t, J=7.6 Hz, 1H), 4.51 (s, 3H), 3.95 (s, 3H). 13C NMR (400 MHz, DMSO-d6) δ 152.9, 147.3, 144.8, 142.2, 141.2, 138.7, 134.8, 128.8, 127.4, 126.6, 126.4, 126.3, 126.0, 122.6, 122.0, 121.8, 120.4, 119.7, 119.1, 116.0, 115.0, 109.8, 109.7, 44.3, 29.3. HRMS (MALDI-TOF) m/z Calcd for C25H21N2 349.1699. Found 349.1694 [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

Sources & evidence

ORD record
ord-d63f440c6e7f46e48b4b1629ea8b6f4b
Source dataset
uspto-grants-2015_10
Patent number
US09156814B2

Reaction notes

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