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

HRID 864573Notes

Reaction equation

HRID 864573 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-0d12f6c78058469f975c4409328253f0
Source dataset
uspto-grants-1996_10
Patent number
US05563162

Reaction notes

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