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

HRID 365124

Reaction equation

HRID 365124 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].[CH2:21]([N:23]([CH2:32][CH3:33])[C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[O:29])=[CH:26][CH:25]=1)[CH3:22].N1CCCCC1.CCOCC>C(O)C>[OH2:29].[Br-:1].[CH2:32]([N:23]([CH2:21][CH3:22])[C:24]1[CH:31]=[CH:30][C:27]([CH:28]=[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:26][CH:25]=1)[CH3:33].[CH2:21]([N:23]([C:24]1[CH:25]=[CH:26][C:27]([CH:28]=[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:30][CH:31]=1)[CH2:32][CH3:33])[CH3:22].[Br-:1]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8082PiperidineHCID 671144-(Diethylamino)benzaldehydeHCID 219878411-Dodecyl-2-methylpyridinium bromide

Product 1

HCID 1317148382-[4-(Diethylamino)styryl]-1-dodecylpyridinium bromide hemihydrateYield 41.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Dodecyl-2-methylpyridinium bromide (3.42 g), 0.01 mole) and 4-diethylaminobenzaldehyde (1.9 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-(diethylamino)styryl]-1-dodecylpyridinium bromide hemihydrate, (2.1 g), melting point 199°-200° C.

Workup

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

Sources & evidence

ORD record
ord-940de61dbdf347a2848357fa33583c82
Source dataset
uspto-grants-1986_08
Patent number
US04608379

Linked notes

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