Phenethylamine → Methyl phenethylcarbamate

HRID 323691

Reaction equation

HRID 323691 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].C(OCC)C>C1COCC1>[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

6

Reactant 4

HCID 1001PhenethylamineHCID 3283Diethyl EtherHCID 6586Methyl chloroformateHCID 8471Triethylamine

Product 1

HCID 4380476Methyl phenethylcarbamateYield 95%

Reagents, catalysts & solvents 1

HCID 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 1 N HC1 (800 mL) was added. The organic layer was washed with water, dried (MgSO4), and 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. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-277c8eda734142b89fd4a03135086a4c
Source dataset
uspto-grants-2001_04
Patent number
US06214841B1

Linked notes

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