N-(4-methoxybenzyl)-N,N-bis[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]amine → N,N-bis[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]amine

HRID 68623Notes

Reaction equation

COC1C=CC(C[N:8]([CH2:23][C:24]2[N:25]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH:26]=[CH:27][N:28]=2)[CH2:9][C:10]2[N:11]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:12]=[CH:13][N:14]=2)=CC=1>C(O)C.[C+4].[OH-].[Pd+2].[OH-].[OH-].[OH-].[OH-].[OH-]>[CH3:20][Si:19]([CH3:22])([CH3:21])[CH2:18][CH2:17][O:16][CH2:15][N:11]1[CH:12]=[CH:13][N:14]=[C:10]1[CH2:9][NH:8][CH2:23][C:24]1[N:25]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH:26]=[CH:27][N:28]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of the compound 1 (665 mg) in ethanol (5 mL), 20% palladium hydroxide carbon (500 mg) was added under an argon atmosphere. The reaction mixture was stirred under a hydrogen gas atmosphere at 65° C. for 3 hours. The reaction mixture was filtered through Celite (trade name) and then concentrated. The obtained residue was purified by silica gel column chromatography (dichloromethane:methanol:28% ammonia water=10:1:0→80:10:1) to obtain the title compound (467 mg) having the following physical properties.

Workup

filtrationThe reaction mixture was filtered through Celite (trade name)
concentrationconcentrated
customThe obtained residue was purified by silica gel column chromatography (dichloromethane:methanol:28% ammonia water=10:1:0→80:10:1)

Sources & evidence

ORD record: ord-07c16e1a070943b18d4dcd57d8ea5ee1
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822459B2

Reaction notes

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