HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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 68623
Notes
Print preview

Reaction equation

HRID 68623 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 67163648N-(4-methoxybenzyl)-N,N-bis[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]amine

Product 1

HCID 67162798N,N-bis[(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)methyl]amineYield 89.5%

Reagents, catalysts & solvents 2

HCID 178420936HCID 178420936, compoundCatalystHCID 702EthanolSolvent

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

  1. filtrationThe reaction mixture was filtered through Celite (trade name)
  2. concentrationconcentrated
  3. 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

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes