Syringaldehyde → 4-[4-(5,6-dihydro-11H-imidazo[2,1-b][3]benzazepin-11-ylidene)-1-piperidinyl]-2,6-dimethoxyphenol

HRID 324297Notes

Reaction equation

HRID 324297 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:12][CH3:13])[C:10]=1[OH:11])C=O.[NH:14]1[CH2:19][CH2:18][C:17](=[C:20]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[CH2:24][CH2:23][N:22]3[CH:31]=[CH:32][N:33]=[C:21]23)[CH2:16][CH2:15]1.[H][H]>CO.S1C=CC=C1.[Pd]>[N:33]1[CH:32]=[CH:31][N:22]2[CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:20](=[C:17]3[CH2:18][CH2:19][N:14]([C:5]4[CH:8]=[C:9]([O:12][CH3:13])[C:10]([OH:11])=[C:3]([O:2][CH3:1])[CH:4]=4)[CH2:15][CH2:16]3)[C:21]=12

Participants

7

Reactant 3

HCID 8655SyringaldehydeHCID 186124926,11-dihydro-11-(4-piperidinylidene)-5H-imidazo[2,1-b][3]benzazepineHCID 178418361HCID 178418361, compound

Product 1

HCID 186124964-[4-(5,6-dihydro-11H-imidazo[2,1-b][3]benzazepin-11-ylidene)-1-piperidinyl]-2,6-dimethoxyphenolYield 67.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8030ThiopheneSolvent

Procedure

A mixture of 3,5-dimethoxy-4-hydroxybenzaldehyde (8 g) and 6,11-dihydro-11-(4-piperidinylidene)-5H-imidazo[2,1-b][3]benzazepine (9 g) in methanol (250 ml) and thiophene (4%, 3 ml) was hydrogenated at room temperature with palladium on activated carbon (10%, 2 g) as a catalyst. After uptake of hydrogen (1 equivalent), the catalyst was filtered off and the filtrate was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5). The pure fractions were collected and evaporated, yielding 9.5 g (65%) of 4-[4-(5,6-dihydro-11H-imidazo[2,1-b][3]benzazepin-11-ylidene)-1-piperidinyl]-2,6-dimethoxyphenol (intermediate 8).

Workup

  1. customthe filtrate was evaporated
  2. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5)
  3. customThe pure fractions were collected
  4. customevaporated

Sources & evidence

ORD record
ord-579eba0ff0eb4702bb42d7379da454c3
Source dataset
uspto-grants-2001_04
Patent number
US06218381B1

Reaction notes

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