Diisopropyl Ether → 2-[4-(Diethylamino)styryl]-5-ethyl-1-propylpyridinium bromide hemihydrate

HRID 365119Notes

Reaction equation

HRID 365119 reaction equation
[Br-:1].[CH2:2]([C:4]1[CH:5]=[CH:6][C:7]([CH3:13])=[N+:8]([CH2:10][CH2:11][CH3:12])[CH:9]=1)[CH3:3].[CH2:14]([N:16]([CH2:25][CH3:26])[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1)[CH3:15].N1CCCCC1.C(OC(C)C)(C)C>CO.C(O)(C)C.CCOCC>[OH2:22].[Br-:1].[CH2:25]([N:16]([CH2:14][CH3:15])[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[CH:13][C:7]2[CH:6]=[CH:5][C:4]([CH2:2][CH3:3])=[CH:9][N+:8]=2[CH2:10][CH2:11][CH3:12])=[CH:19][CH:18]=1)[CH3:26].[CH2:14]([N:16]([C:17]1[CH:18]=[CH:19][C:20]([CH:21]=[CH:13][C:7]2[CH:6]=[CH:5][C:4]([CH2:2][CH3:3])=[CH:9][N+:8]=2[CH2:10][CH2:11][CH3:12])=[CH:23][CH:24]=1)[CH2:25][CH3:26])[CH3:15].[Br-:1]

Participants

8

Reactant 4

HCID 7914Diisopropyl EtherHCID 8082PiperidineHCID 671144-(Diethylamino)benzaldehydeHCID 133894285-Ethyl-2-methyl-1-propylpyridinium bromide

Product 1

HCID 704551732-[4-(Diethylamino)styryl]-5-ethyl-1-propylpyridinium bromide hemihydrateYield 12.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×HCID 3776IsopropanolSolvent2×

Procedure

5-Ethyl-2-methyl-1-propylpyridinium bromide (7.32 g, 0.03 mole) and 4-diethylaminobenzaldehyde (7.0 g, 0.04 mole) were refluxed for four hours in methanol (50 ml) in the presence of piperidine (1 ml) under nitrogen. On cooling and addition of ether no precipitate was obtained. The solution was evaporated to give a red oil which was dissolved in isopropanol and twice the volume of ether was added, when a red crystalline solid was obtained (5.4 g). 2 Grams were re-dissolved in isopropanol and isopropyl ether was added to give red crystals of 2-[4-(diethylamino)styryl]-5-ethyl-1-propylpyridinium bromide hemihydrate (1.6 g), melting point 165°-167° (decomposition).

Workup

  1. temperatureOn cooling
  2. customwas obtained
  3. customThe solution was evaporated
  4. customto give a red oil which
  5. customwhen a red crystalline solid was obtained (5.4 g)

Sources & evidence

ORD record
ord-cb54cf80e49b4a9f8b6db21eca512b2c
Source dataset
uspto-grants-1986_08
Patent number
US04608379

Reaction notes

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