Triethylsilane → N,N-Dimethyl-4-((5-methyl-1H-imidazol-4-yl)methyl)naphthalen-1-amine

HRID 907513Notes

Reaction equation

HRID 907513 reaction equation
[CH3:1][N:2]([CH3:40])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]([C:15]2[N:19](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:18]=[N:17][C:16]=2[CH3:39])[OH:14])=[CH:5][CH:4]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[CH3:40][N:2]([CH3:1])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH2:13][C:15]2[N:19]=[CH:18][NH:17][C:16]=2[CH3:39])=[CH:5][CH:4]=1.[CH3:1][N:2]([CH3:40])[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]([CH:13]([C:15]2[N:19]=[CH:18][NH:17][C:16]=2[CH3:39])[OH:14])=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 67026330(4-(dimethylamino)naphthalen-1-yl)(4-methyl-1-trityl-1H-imidazol-5-yl)methanol

Product 2

HCID 25004152N,N-Dimethyl-4-((5-methyl-1H-imidazol-4-yl)methyl)naphthalen-1-amineYield 32%HCID 57965652(4-(dimethylamino)naphthalen-1-yl)(5-methyl-1H-imidazol-4-yl)methanolYield 25%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (4) (3.35 g, 6.40 mmol) in TFA (30 mL) was added triethylsilane (6 mL, 38.4 mmol). The reaction mixture was stirred at room temperature overnight. TFA was removed under vacuum. The residue was basified with 2 M sodium hydroxide to pH>7. The aqueous layer was extracted three times with chloroform/isopropanol (3:1200 mL). The pooled organic layers were dried over magnesium sulfate. The mixture was filtered and the solvents were removed under vacuum. The residue was purified by chromatography on silica gel with 2 to 5% saturated ammonia methanol in dichloromethane to give N,N-dimethyl-4-((5-methyl-1H-imidazol-4-yl)methyl)naphthalen-1-amine (5) (0.55 g, 2.07 mmol, 32% yield), and (4-(dimethylamino)naphthalen-1-yl)(5-methyl-1H-imidazol-4-yl)methanol (6) (0.45 g, 1.60 mmol, 25% yield).

Workup

  1. customTFA was removed under vacuum
  2. extractionThe aqueous layer was extracted three times with chloroform/isopropanol (3:1200 mL)
  3. dry with materialThe pooled organic layers were dried over magnesium sulfate
  4. filtrationThe mixture was filtered
  5. customthe solvents were removed under vacuum
  6. customThe residue was purified by chromatography on silica gel with 2 to 5% saturated ammonia methanol in dichloromethane

Sources & evidence

ORD record
ord-be0cefc1f759453ab0c14f1f5ca7b4a4
Source dataset
uspto-grants-2011_09
Patent number
US08013169B2

Reaction notes

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