Methyl chloroformate → HCID 68473066, compound

HRID 387687Notes

Reaction equation

HRID 387687 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][NH:11][CH:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+].Cl[C:26]([O:28][CH3:29])=[O:27]>O1CCCC1>[CH3:29][O:28][C:26](=[O:27])[N:11]([CH2:10][CH2:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[Br:1])[CH:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 68473149HCID 68473149, compound

Product 1

HCID 68473066HCID 68473066, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.045 g of N-[2-(2-bromo-4-fluorophenyl)ethyl]heptan-4-amine in solution in 15 cm3 of anhydrous tetrahydrofuran and 502 mg of potassium carbonate are stirred under an inert atmosphere at a temperature in the vicinity of 20° C. 0.28 cm3 of methyl chloroformate is introduced over 10 min using a syringe. The reaction mixture is brought to reflux over 30 h, then filtered through celite and then concentrated using a rotary evaporator under reduced pressure (5 kPa). The residual oil is put into solution in 20 cm3 of dichloromethane. The organic phase is washed successively with 10 cm3 of an aqueous solution of hydrochloric acid (pH=2), then 3×20 cm3 of distilled water. The organic phase is then dried, then concentrated to dryness using a rotary evaporator under reduced pressure (5 kPa). The residual oil is taken up with 10 cm3 of diisopropyl ether. The solid which appears is filtered and the filtrate is concentrated to dryness using a rotary evaporator under reduced pressure (5 kPa) in order to result in 778 mg of methyl[2-(2-bromo-4-fluorophenyl)ethyl](1-propylbutyl)carbamate in the form of a beige oil.

Workup

  1. temperatureto reflux over 30 h
  2. filtrationfiltered through celite
  3. concentrationconcentrated
  4. customa rotary evaporator under reduced pressure (5 kPa)
  5. washThe organic phase is washed successively with 10 cm3 of an aqueous solution of hydrochloric acid (pH=2)
  6. customThe organic phase is then dried
  7. concentrationconcentrated to dryness
  8. customa rotary evaporator under reduced pressure (5 kPa)
  9. filtrationThe solid which appears is filtered
  10. concentrationthe filtrate is concentrated to dryness
  11. customa rotary evaporator under reduced pressure (5 kPa) in order
  12. customto result in 778 mg of methyl[2-(2-bromo-4-fluorophenyl)ethyl](1-propylbutyl)carbamate in the form of a beige oil

Sources & evidence

ORD record
ord-7761924bc25441adb1d86310f2992a4e
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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