Hydrochloric Acid → benzyl N-phenyl-N-(prop-2-en-1-yl)carbamate

HRID 1351849Notes

Reaction equation

HRID 1351849 reaction equation
[CH2:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:2]=[CH2:3].N1C=CC=CC=1.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].Cl>ClCCl>[CH2:1]([N:4]([C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 10387Benzyl chloroformateHCID 68525N-Allylaniline

Product 1

HCID 11448535benzyl N-phenyl-N-(prop-2-en-1-yl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, to a solution of allylphenylamine (3 ml) in dichloromethane (30 ml) were added pyridine (2.1 ml) and benzyl chloroformate (3.5 ml) at 5° C., and the mixture was stirred at the same temperature for 3 hours. The resulting mixture was poured into aqueous 1N hydrogen chloride and extracted with ethyl acetate. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=20:1 to 10:1) to give N-allyl-N-phenylbenzyloxycarbonylamine (5.5 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=20:1 to 10:1)

Sources & evidence

ORD record
ord-bec41db155af49279ba52e166026ea5b
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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