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

HRID 365123

Reaction equation

HRID 365123 reaction equation
[Br-:1].[CH2:2]([N+:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH3:21][N:22]([CH3:31])[C:23]1[CH:30]=[CH:29][C:26]([CH:27]=O)=[CH:25][CH:24]=1.N1CCCCC1.CCOCC>C(O)C>[Br-:1].[CH3:21][N:22]([CH3:31])[C:23]1[CH:30]=[CH:29][C:26]([CH:27]=[CH:20][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N+:14]=2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 74794-(Dimethylamino)BenzaldehydeHCID 8082PiperidineHCID 219878411-Dodecyl-2-methylpyridinium bromide

Product 1

HCID 704553152-[4-(Dimethylamino)styryl]-1-dodecylpyridinium bromideYield 50.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Dodecyl-2-methylpyridinium bromide (3.42 g, 0.01 mole) and 4-dimethylaminobenzaldehyde (1.6 g, 0.011 mole) were refluxed in ethanol (15 ml) in the presence of piperidine (0.2 ml) under nitrogen for two hours. The solution was cooled and ether was added when an orange solid crystallised which was collected giving 2-[4-(dimethylamino)styryl]-1-dodecylpyridinium bromide quarter hydrate (2.4 g), melting point 197°-198° C.

Workup

  1. temperatureThe solution was cooled
  2. customcrystallised which
  3. customwas collected

Sources & evidence

ORD record
ord-e93c4077a2d647a38d8aceb4ff11183f
Source dataset
uspto-grants-1986_08
Patent number
US04608379

Linked notes

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