Benzylethanolamine → 2-[Benzyl(2-methylprop-2-EN-1-YL)amino]ethan-1-OL

HRID 601560Notes

Reaction equation

HRID 601560 reaction equation
[CH2:1](Cl)[C:2](=[CH2:4])[CH3:3].[CH2:6]([NH:13][CH2:14][CH2:15][OH:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH2:6]([N:13]([CH2:3][C:2]([CH3:4])=[CH2:1])[CH2:14][CH2:15][OH:16])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 4348BenzylethanolamineHCID 112413-Chloro-2-methyl-1-propeneHCID 11430Potassium Carbonate

Product 1

HCID 574215002-[Benzyl(2-methylprop-2-EN-1-YL)amino]ethan-1-OLYield 96.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
62 °C

Procedure

Add methallyl chloride (68.8 g, 0.760 mol, Aldrich) to a mixture of N-benzylethanolamine (100 g, 0.663 mol) and potassium carbonate (139 g, 1.00 mol) in water (600 mL). Heat the mixture to 62° C. for 23 h and then transfer to a separatory funnel. Extract the product with tert-butyl methyl ether (500 mL). Dry, filter, and concentrate the organic solution to give the title compound (131 g, 96%) as a colorless liquid. 1H NMR (DMSO-d6, 400 MHz) δ 7.20-7.33 (5H, m), 4.92 (1H, br s), 4.83 (1H, br s), 4.35 (1H, t), 3.53 (2H, s), 3.44-3.50 (2H, m), 2.94 (1H, s), 2.42 (2H, t), 1.69 (1H, s).

Workup

  1. customtransfer to a separatory funnel
  2. extractionExtract the product with tert-butyl methyl ether (500 mL)
  3. customDry
  4. filtrationfilter
  5. concentrationconcentrate the organic solution

Sources & evidence

ORD record
ord-21384796dfdf4649b743bc624bbbf8ba
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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