Phenethylamine → Ethyl phenethylcarbamate

HRID 2042121Notes

Reaction equation

HRID 2042121 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([O-])([O-])=O.[Na+].[Na+].Cl[C:17]([O:19][CH2:20][CH3:21])=[O:18]>CCOC(C)=O>[CH2:1]([NH:9][C:17](=[O:18])[O:19][CH2:20][CH3:21])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 10340Sodium CarbonateHCID 10928Ethyl chloroformate

Product 1

HCID 247630Ethyl phenethylcarbamate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of phenethylamine (60.5 g, 0.5 mol) and Na2CO3 (63.6 g, 0.6 mol) in EtOAc/HO (800 mL, 4:1) was added ethyl chloroformate, dropwise, (65.1 g, 0.6 mol) at 0° C. during a period of 1 h. The mixture was warmed to RT and stirred for an additional 1 h. The organic phase was separated and the aqueous layer was extracted with EtOAc. The combined organic phases were washed with H2O and brine, dried (Na2SO4), concentrated in vacuo and purified by flash chromatography to afford ethyl phenethylcarbamate (90.2 g). 1H NMR (400 MHz, CDCl3) δ 7.32-7.18 (m, 5H), 4.73 (brs, 1H), 4.14-4.08 (q, J=6.8 Hz, 2H), 3.44-3.43 (m, 2H), 2.83-2.79 (t, J=6.8 Hz, 2H), 1.26-1.21 (t, J=6.8 Hz, 3H).

Workup

  1. customThe organic phase was separated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe combined organic phases were washed with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-5d8f9d1972374337add4c3d4416dc8c3
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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