Methyl chloroformate → methyl N-[2-(3-methoxyphenyl)ethyl]carbamate

HRID 492633Notes

Reaction equation

HRID 492633 reaction equation
CO[NH:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C1C[O:15][CH2:14]C1.CCN(CC)CC.Cl[C:25]([O:27][CH3:28])=[O:26]>C(OCC)(=O)C.O>[CH3:28][O:27][C:25](=[O:26])[NH:3][CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([O:15][CH3:14])[CH:11]=1

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 121190Methoxyphenylethylamine

Product 1

HCID 13948245methyl N-[2-(3-methoxyphenyl)ethyl]carbamateYield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine Methoxyphenylethylamine (9.6 ml, 66.1 mmol), THF (300 mmol), Et3N (11.0 ml, 78.9 mmol), and methyl chloroformate (26.0 ml, 339 mmol) at 0° C. under nitrogen atmosphere. After the reaction stirs at room temperature for 18 hours, add the mixture into water, wash with brine, and dry the organic layer over Na2SO4 followed by concentrating under reduced pressure. Flash chromatograph using 2:1 Hexanes:Ethyl acetate to afford 13.6 g, 65.0 mmol (98% yield) of the title compound: 1H NMR (500 MHz, CDCl3); 2.8 (2H, t, J=6.7, 7.0 Hz), 3.41-3.46 (2H, m), 3.7 (3H, s), 3.8 (3H, s), 4.6-4.8 (1H, b s), 6.7-6.8 (3H, m), 7.2-7.3 (1H, m); MS m/z 210 (M+1).

Workup

  1. customat 0° C.
  2. washwash with brine
  3. dry with materialdry the organic layer over Na2SO4
  4. concentrationby concentrating under reduced pressure

Sources & evidence

ORD record
ord-3dfcf9727eb847cda7c240713834c3ca
Source dataset
uspto-grants-2009_05
Patent number
US07531557B2

Reaction notes

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