Methyl chloroformate → Methyl[2-(2-bromophenyl)ethyl](1-propylbutyl)carbamate

HRID 387620Notes

Reaction equation

HRID 387620 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:10][CH:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14].C(N(CC)CC)C.Cl[C:26]([O:28][CH3:29])=[O:27].[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[CH3:29][O:28][C:26](=[O:27])[N:10]([CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1])[CH:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 68471618N-[2-(2-bromophenyl)ethyl]heptan-4-amine

Product 1

HCID 68474717Methyl[2-(2-bromophenyl)ethyl](1-propylbutyl)carbamate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

5.85 g of N-[2-(2-bromophenyl)ethyl]heptan-4-amine in solution in 60 cm3 of anhydrous tetrahydrofuran are stirred under an inert atmosphere at 0° C. 2.76 cm3 of triethylamine are added to the reaction mixture, then 1.52 cm3 of methyl chloroformate are introduced over 10 min using a syringe. The reaction mixture is kept stirring for 1 h at 0° C., then 3 h at 20° C. 20 cm3 of a saturated aqueous solution of ammonium chloride are added, then 100 cm3 of ethyl acetate. The organic phase is washed with 4 lots of 30 cm3 of water, then 30 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, filtered through a pellet (30 g) of silica (particle size: 40-63 μm), rinsed with 50 cm3 of ethyl acetate and concentrated using a rotary evaporator under reduced pressure (5 kPa). 6.4 g of methyl[2-(2-bromophenyl)ethyl](1-propylbutyl)carbamate are obtained in the form of a colorless oil.

Workup

  1. custom3 h
  2. customat 20° C
  3. washThe organic phase is washed with 4 lots of 30 cm3 of water
  4. dry with material30 cm3 of a saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  5. filtrationfiltered through a pellet (30 g) of silica (particle size: 40-63 μm)
  6. washrinsed with 50 cm3 of ethyl acetate
  7. concentrationconcentrated
  8. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-fec35d9094ee4243b58b838e8e0eb68b
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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