Piperidine → 2-[4-(Diethylamino)styryl]-1-hexylpyridinium bromide hemihydrate
Reaction equation
[Br-:1].[CH2:2]([N+:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:14])[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH2:15]([N:17]([CH2:26][CH3:27])[C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[O:23])=[CH:20][CH:19]=1)[CH3:16].N1CCCCC1>CO>[OH2:23].[Br-:1].[CH2:26]([N:17]([CH2:15][CH3:16])[C:18]1[CH:25]=[CH:24][C:21]([CH:22]=[CH:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][N+:8]=2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:20][CH:19]=1)[CH3:27].[CH2:15]([N:17]([C:18]1[CH:19]=[CH:20][C:21]([CH:22]=[CH:14][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][N+:8]=2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])=[CH:24][CH:25]=1)[CH2:26][CH3:27])[CH3:16].[Br-:1]Participants
5
Procedure
1-Hexyl-2-methylpyridinium bromide (7.8 g, 0.03 mole) and 4-diethylaminobenzaldehyde (7.0 g, 0.04 mole) were refluxed in methanol (50 ml) in the presence of piperidine (1.0 ml) under nitrogen for four hours. The solution was evaporated and the resulting oil was redissolved in a small amount of isopropanol. Addition of twice the volume of ether gave a red crystalline solid which was collected and washed with isopropanol/ether to give 2-[4-(diethylamino)styryl]-1-hexylpyridinium bromide hemihydrate (5.8 g), melting point 222°-223° (decomposition).
Workup
- customThe solution was evaporated
- dissolutionthe resulting oil was redissolved in a small amount of isopropanol
- additionAddition of twice the volume of ether
- customgave a red crystalline solid which
- customwas collected
- washwashed with isopropanol/ether
Sources & evidence
- ORD record
- ord-309cd08193b94334b1b909faff8e5a58
- Source dataset
- uspto-grants-1986_08
- Patent number
- US04608379
Reaction notes
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