Methyl chloroformate → Methyl benzyl[2-(2-bromophenyl)ethyl]carbamate

HRID 387632Notes

Reaction equation

HRID 387632 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Br:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:26]([O:28][CH3:29])=[O:27].C(OCC)(=O)C>O1CCCC1.O>[CH2:1]([N:8]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Br:17])[C:26](=[O:27])[O:28][CH3:29])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 11055371N-benzyl-2-(2-bromophenyl)ethanamine

Product 1

HCID 68470524Methyl benzyl[2-(2-bromophenyl)ethyl]carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2.48 g of N-benzyl-2-(2-bromophenyl)ethanamine in solution in 50 cm3 of anhydrous tetrahydrofuran are stirred under an inert atmosphere at 0° C. 1.2 cm3 of triethylamine are added to the reaction mixture, then 0.67 cm3 of methyl chloroformate is introduced using a syringe. The reaction mixture is kept stirring for 1 h at 0° C., then 5 h at a temperature close to 20° C. The reaction mixture is poured into a mixture containing ice, ethyl acetate and water. Stirring is continued for 10 min. The aqueous phase is extracted with ethyl acetate. The organic phases are combined, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, then concentrated using a rotary evaporator under reduced pressure (5 kPa). The brown oil obtained is purified by flash chromatography over silica (column: 200 g; particle size: 15-40 μm; eluent: 70% cyclohexane/30% ethyl acetate). After concentrating the fractions under reduced pressure, 2.51 g of methyl benzyl[2-(2-bromophenyl)ethyl]carbamate are obtained in the form of an oil.

Workup

  1. custom5 h at a temperature close to 20° C
  2. additionThe reaction mixture is poured into a mixture
  3. stirringStirring
  4. waitis continued for 10 min
  5. extractionThe aqueous phase is extracted with ethyl acetate
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customa rotary evaporator under reduced pressure (5 kPa)
  10. customThe brown oil obtained
  11. customis purified by flash chromatography over silica (column: 200 g; particle size: 15-40 μm; eluent: 70% cyclohexane/30% ethyl acetate)
  12. concentrationAfter concentrating the fractions under reduced pressure, 2.51 g of methyl benzyl[2-(2-bromophenyl)ethyl]carbamate
  13. customare obtained in the form of an oil

Sources & evidence

ORD record
ord-43ed88a4ae544eb49999c56a663cdd18
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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