Piperidine → HCID 70576684, compound

HRID 1577288

Reaction equation

HRID 1577288 reaction equation
[I-:1].[CH3:2][N+:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH3:9].[CH3:10][O:11][CH:12]([O:23][CH3:24])[CH2:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=1.N1CCCCC1>CO>[I-:1].[CH3:2][N+:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=[CH:19][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][CH:12]([O:23][CH3:24])[O:11][CH3:10])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 701071,2-Dimethylpyridinium iodideHCID 20572032HCID 20572032, compound

Product 1

HCID 70576684HCID 70576684, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 50 ml of methanol, 12.7 g of 1,2-dimethylpyridinium iodide and 11.96 g of p-(2,2-dimethoxyethoxy)benzaldehyde were dissolved. The resultant solution, with 1 ml of piperidine added thereto, was refluxed for five hours. The solution was left to cool and the crystals which consequently deposited in the solution were collected through filtration and thoroughly washed with acetone. Consequently, there was obtained 16.30 g of 1-methyl-2[p-(2,2-dimethoxyethoxy)-styryl]pyridinium iodide. In water, this product showed the highest absorption at 360 nm (ε=2.67×104). The infrared absorption spectrum (KBr) of the product showed peaks at 1630, 1615, 1595, 1568, 1512, 1450, 1298, 1260, 1180, 1140, 1073, 965, 862, 821 and 776 cm-1. The yield was 67%.

Workup

  1. temperaturewas refluxed for five hours
  2. waitThe solution was left
  3. temperatureto cool
  4. filtrationwere collected through filtration
  5. washthoroughly washed with acetone

Sources & evidence

ORD record
ord-72bc878b0a964798bd0c73169da3ba30
Source dataset
uspto-grants-1981_09
Patent number
US04287335

Linked notes

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