Diethyl Ether → 1-Dodecyl-2-[(4-piperidino)styryl]pyridinium bromide

HRID 365127Notes

Reaction equation

HRID 365127 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].[N:21]1([C:27]2[CH:34]=[CH:33][C:30]([CH:31]=O)=[CH:29][CH:28]=2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.N1CCCCC1.CCOCC>CO>[Br-:1].[CH2:2]([N+:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH:20]=[CH:31][C:30]1[CH:29]=[CH:28][C:27]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:34][CH:33]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8082PiperidineHCID 2913544-(Piperidin-1-yl)benzaldehydeHCID 219878411-Dodecyl-2-methylpyridinium bromide

Product 1

HCID 704551531-Dodecyl-2-[(4-piperidino)styryl]pyridinium bromideYield 24.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Dodecyl-2-methylpyridinium bromide (2.3 g, 0.0067 mole) and 4-piperidinobenzaldehyde (1.27 g, 0.0067 mole) were refluxed in methanol (20 ml) in the presence of piperdine (0.1 ml) under nitrogen for three hours. The solution was cooled and addition of ether gave a crystalline solid which was collected giving 1-dodecyl-2-[(4-piperidino)styryl]pyridinium bromide (0.85 g), melting point 203°-205° C.

Workup

  1. temperatureThe solution was cooled
  2. customgave a crystalline solid which
  3. customwas collected

Sources & evidence

ORD record
ord-8c2c0cba5a8949d388c880a375e24e4b
Source dataset
uspto-grants-1986_08
Patent number
US04608379

Reaction notes

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