Triethylamine → (4-Bromo-3-methyl-phenyl)-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-amine

HRID 1755019Notes

Reaction equation

HRID 1755019 reaction equation
C(N(CC)CC)C.[C:8]([Si:12]([CH3:15])([CH3:14])Cl)([CH3:11])([CH3:10])[CH3:9].[Br:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][CH2:24][CH2:25][OH:26])=[CH:19][C:18]=1[CH3:27]>ClCCl.CN(C1C=CC=CN=1)C>[Br:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][CH2:24][CH2:25][O:26][Si:12]([C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:15])[CH3:14])=[CH:19][C:18]=1[CH3:27]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 285749422-[(4-Bromo-3-methylphenyl)amino]ethan-1-ol

Product 1

HCID 66816772(4-Bromo-3-methyl-phenyl)-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-amineYield 98%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (0.39 ml, 2.80 mmol), dimethylaminopyridine (13 mg, 0.11 mmol) and tert-butyl-dimethyl-chloro-silane (319 mg, 2.11 mmol) were added to a solution of 2-(4-bromo-3-methyl-phenylamino)-ethanol (430 mg, 1.87 mmol) in dichloromethane (3.8 ml) at room temperature, and the mixture was stirred at room temperature for 24 hours. The reaction mixture was diluted with dichloromethane, and the organic layer was washed with water, dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give (4-bromo-3-methyl-phenyl)-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-amine (629 mg, 98%).

Workup

  1. washthe organic layer was washed with water
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-f70f60b7ea4840e4aec79452d63eb3c6
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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