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

HRID 552364Notes

Reaction equation

HRID 552364 reaction equation
[CH3:1][Si:2]([CH3:15])([CH3:14])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[CH:11]=[CH:10][N:9]=[C:8]1[CH:12]=O.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][NH2:25])=[CH:20][CH:19]=1.C(O[BH-](O[C:36](=[O:38])[CH3:37])OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCl>[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]([CH2:12][C:8]2[N:7]([CH2:6][O:38][CH2:36][CH2:37][Si:2]([CH3:1])([CH3:14])[CH3:3])[CH:11]=[CH:10][N:9]=2)[CH2:12][C:8]2[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:15])([CH3:14])[CH3:1])[CH:11]=[CH:10][N:9]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 754524-MethoxybenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 136002351-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carbaldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-({[2-(trimethylsilyl)ethyloxy]methyl}-1H-imidazole-2-carboaldehyde (CAS Registry Number: 101226-42-0, 1.5 g) and {[4-(methyloxy)phenyl]methyl}amine (0.39 mL) in dichloromethane (containing 1% acetic acid) (10 mL), sodium triacetoxyborohydride (1.91 g) was added. The reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was added by an aqueous 1 N sodium hydroxide solution and then extracted with dichloromethane. The extract thus obtained was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol:triethylamine=1:0:0→10:1:0→10:1:0.1) to obtain the title compound (1.71 g) having the following physical properties.

Workup

  1. extractionextracted with dichloromethane
  2. extractionThe extract thus
  3. customobtained
  4. washwas washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:methanol:triethylamine=1:0:0→10:1:0→10:1:0.1)

Sources & evidence

ORD record
ord-c6dfcafea70d4c20ad62553d6be61762
Source dataset
uspto-grants-2011_05
Patent number
US07951816B2

Reaction notes

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