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

HRID 228479Notes

Reaction equation

HRID 228479 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-f675648c005047d6a123c4b8b695e0c1
Source dataset
uspto-grants-2009_07
Patent number
US07560463B2

Reaction notes

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