Imidazole → 2-(tert-butyldiphenylsilyloxy)-N-methylethanamine

HRID 564923

Reaction equation

HRID 564923 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].N1C=CN=C1.[Si:11](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CN(C)C=O.O>[Si:11]([O:5][CH2:4][CH2:3][NH:2][CH3:1])([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 80162-(Methylamino)ethanolHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 118231582-(tert-butyldiphenylsilyloxy)-N-methylethanamineYield 31.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-methylethanolamine (600 mg), in N,N-dimethylformamide were added imidazole (1.13 g) and tert-butyldiphenylsilyl chloride (2.20 g) at ambient temperature with stirring. After 8 hours, the mixture was diluted with water (60 ml) and was extracted with ethyl acetate (20 ml) twice. The organic layer was washed with water three times and brine, dried over magnesium sulfate. The solvent was removed in vacuo. The residue was purified by column chromatography eluting with dichloromethane-methanol to give N-(2-tert-butyldiphenylsilyloxyethyl)-N-methylamine (780 mg) as an oil.

Workup

  1. extractionwas extracted with ethyl acetate (20 ml) twice
  2. washThe organic layer was washed with water three times and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by column chromatography
  6. washeluting with dichloromethane-methanol

Sources & evidence

ORD record
ord-12efae263eca4be991f2e94a41bf1af9
Source dataset
uspto-grants-2001_01
Patent number
US06169095A

Linked notes

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