Piperidine → HCID 70577732, compound

HRID 1577289Notes

Reaction equation

HRID 1577289 reaction equation
[I-:1].[CH3:2][N+:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH3:13].[CH3:14][O:15][CH:16]([O:27][CH3:28])[CH2:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1.N1CCCCC1>CO>[I-:1].[CH3:2][N+:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH:13]=[CH:23][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH2:17][CH:16]([O:27][CH3:28])[O:15][CH3:14])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 27504451,2-Dimethylquinolinium iodideHCID 20572032HCID 20572032, compound

Product 1

HCID 70577732HCID 70577732, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 20 ml of methanol, 4.28 g of 1,2-dimethylquinolinium iodide and 3.47 g of p-(2,2-dimethoxyethoxy)benzaldehyde were dissolved. The resultant solution, with 0.3 ml of piperidine added thereto, was refluxed for seven hours. The solution was left to cool. The crystals which consequently deposited were collected through filtration and then washed thoroughly with acetone. Consequently, there was obtained 5.03 g of 1-methyl-2-[p-(2,2-dimethoxyethoxy)-styryl]quinolinium iodide which boiled at 209°~212° C. This product in water showed absorption bands (λmax) at 224, 255, 307 and 399 nm. The infrared absorption spectrum (KBr) showed peaks at 1610, 1590, 1572, 1516, 1240, 1180, 1130, 1068, 985, 830, 780 and 760 cm-1.

Workup

  1. temperaturewas refluxed for seven hours
  2. waitThe solution was left
  3. temperatureto cool
  4. filtrationThe crystals which consequently deposited were collected through filtration
  5. washwashed thoroughly with acetone

Sources & evidence

ORD record
ord-d3525303220a497a8b7fb5e8686c6147
Source dataset
uspto-grants-1981_09
Patent number
US04287335

Reaction notes

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