Diethyl Ether → 2-[4-(Dimethylamino)-styryl]-5-ethyl-1-propylpyridinium bromide

HRID 365120Notes

Reaction equation

HRID 365120 reaction equation
[Br-:1].[CH2:2]([C:4]1[CH:5]=[CH:6][C:7]([CH3:13])=[N+:8]([CH2:10][CH2:11][CH3:12])[CH:9]=1)[CH3:3].[CH3:14][N:15]([CH3:24])[C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1.N1CCCCC1.CCOCC>CO>[Br-:1].[CH3:14][N:15]([CH3:24])[C:16]1[CH:23]=[CH:22][C:19]([CH:20]=[CH:13][C:7]2[CH:6]=[CH:5][C:4]([CH2:2][CH3:3])=[CH:9][N+:8]=2[CH2:10][CH2:11][CH3:12])=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 74794-(Dimethylamino)BenzaldehydeHCID 8082PiperidineHCID 133894285-Ethyl-2-methyl-1-propylpyridinium bromide

Product 1

HCID 704548882-[4-(Dimethylamino)-styryl]-5-ethyl-1-propylpyridinium bromideYield 62.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Ethyl-2-methyl-1-propylpyridinium bromide (8.1 g, 0.033 mole) and 4-dimethylaminobenzaldehyde (6.0 g, 0.04 mole) were refluxed in methanol (50 ml) in the presence of piperidine (1.5 ml) under nitrogen for four hours. Ether was added to the cool solution and, on scratching, a red solid crystallised which was collected and washed with a little isopropanol to give 2-[4-(dimethylamino)-styryl]-5-ethyl-1-propylpyridinium bromide (7.7 g). Melting point 236°-237° (decomposition).

Workup

  1. customa red solid crystallised which
  2. customwas collected
  3. washwashed with a little isopropanol

Sources & evidence

ORD record
ord-a194a605e7c94849a1f9d517a73e678e
Source dataset
uspto-grants-1986_08
Patent number
US04608379

Reaction notes

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