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

HRID 131026Notes

Reaction equation

HRID 131026 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%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine Methoxyphenylethylamine (9.6 ml, 66.1 mmol), THF (300 ml), 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-0aabe22ece1d4c3e873de3e7545c59b9
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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