Hydrochloric Acid → Methyl phenethylcarbamate

HRID 1593

Reaction equation

HRID 1593 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[C:18]([O:20][CH3:21])=[O:19].Cl>C1COCC1.C(OCC)C>[CH3:21][O:20][C:18]([NH:9][CH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1001PhenethylamineHCID 6586Methyl chloroformateHCID 8471Triethylamine

Product 1

HCID 4380476Methyl phenethylcarbamateYield 95%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of phenethylamine (75.2 mL, 0.6 mol) and triethylamine (83 mL, 0.6 mol) in THF (500 mL) was added slowly methyl chloroformate 46.2 mL, 0.6 mol) dissolved in THF (50 mL). After the reaction was stirred for an additional 1 h at room temperature, diethyl ether (2 L) and 1N HCl (800 mL) were added. The organic layer was washed with water, dried (MgSO4), filtered, and the filtrate was concentrated in vacuo to give a clear oil of pure title compound (102 g, 95%).

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bbd17ea5df144cd0a50c633bd92af129
Source dataset
uspto-grants-1998_03
Patent number
US05726159

Linked notes

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