Diethyl Ether → 2-[4-(Dimethylamino)styryl]-1-hexylpyridinium bromide

HRID 365121Notes

Reaction equation

HRID 365121 reaction equation
[Br-:1].[CH2:2]([N+:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH3:15][N:16]([CH3:25])[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1.N1CCCCC1.CCOCC>CO>[Br-:1].[CH3:15][N:16]([CH3:25])[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[CH:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][N+:8]=2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 74794-(Dimethylamino)BenzaldehydeHCID 8082PiperidineHCID 219878661-Hexyl-2-methylpyridinium bromide

Product 1

HCID 704549972-[4-(Dimethylamino)styryl]-1-hexylpyridinium bromideYield 53.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Hexyl-2-methylpyridinium bromide (7.8 g, 0.03 mole) and 4-dimethylaminobenzaldehyde (6.0 g, 0.04 mole) were refluxed in methanol (50 ml) in the presence of piperidine (1.0 ml) under nitrogen for four hours. On cooling and the addition of about 100 ml of ether a solid crystallised which was collected and washed with a little isopropanol to give 2-[4-(dimethylamino)styryl]-1-hexylpyridinium bromide (6.3 g), melting point 217°-218° (decomposition).

Workup

  1. temperatureOn cooling
  2. customcrystallised which
  3. customwas collected
  4. washwashed with a little isopropanol

Sources & evidence

ORD record
ord-c7dd4cb7b59947ccade8c05c8b1806ec
Source dataset
uspto-grants-1986_08
Patent number
US04608379

Reaction notes

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