Hydrochloric Acid → Methyl phenethylcarbamate

HRID 726661

Reaction equation

HRID 726661 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-643f8e6a65094183ab0d11fd60634a6a
Source dataset
uspto-grants-1998_01
Patent number
US05710130

Linked notes

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