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

HRID 365129Notes

Reaction equation

HRID 365129 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](C)=[CH:3][CH:2]=1.[Br:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[CH3:15][N:16]([CH3:25])[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1.N1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.[CH3:32][CH2:33]OCC>CO>[Br-:8].[CH3:15][N:16]([CH3:25])[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[CH:14][C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][N+:1]=2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])=[CH:19][CH:18]=1

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 74794-(Dimethylamino)BenzaldehydeHCID 79634-MethylpyridineHCID 8082PiperidineHCID 81011-Bromohexane

Product 1

HCID 704553152-[4-(Dimethylamino)styryl]-1-dodecylpyridinium bromide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Picoline (2.79 g, 0.03 mole) and 1-bromohexane (4.25 ml, 0.03 mole) were heated in an oil bath at 130° C. for 2 hours. The resulting brown oil was cooled. Methanol (40 ml), 4-dimethylaminobenzaldehyde (4.5 g, 0.03 mole) and piperdine (0.25 ml) were added. The mixture was refluxed for 3 hours and cooled. A large volume of ether was added to form a crystalline product which was recrystallised by dissolving in isopropyl alcohol and adding ether to give crystals of 4-[4-(dimethylamino)styryl]-1-hexylpyridinium bromide quarter hydrate (2.2 g), melting point 224°-226° C. (decomposition). The compound exhibited infra-red spectral bands at 720, 815, 835, 883, 940, 987, 1158, 1330, 1362, 1522, 1575 and 1640 wavenumbers.

Workup

  1. temperatureThe resulting brown oil was cooled
  2. temperatureThe mixture was refluxed for 3 hours
  3. temperaturecooled
  4. customto form a crystalline product which
  5. customwas recrystallised
  6. dissolutionby dissolving in isopropyl alcohol
  7. additionadding ether

Sources & evidence

ORD record
ord-738d3d00a9964985aa57a459a44247ad
Source dataset
uspto-grants-1986_08
Patent number
US04608379

Reaction notes

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