Allylamine → Benzyl allylcarbamate

HRID 1271090Notes

Reaction equation

HRID 1271090 reaction equation
[CH2:1]([NH2:4])[CH:2]=[CH2:3].C(N(CC)CC)C.[CH2:12]([O:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[CH2:1]([NH:4][C:20](=[O:21])[O:19][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7853AllylamineHCID 8471TriethylamineHCID 10387Benzyl chloroformate

Product 1

HCID 562279Benzyl allylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of allylamine (58 mmoles, 3.34 g) at 0° C. in dichloromethane (100 mL) was added triethylamine (120 mmoles, 16 mL). The mixture was stirred for two minutes, then benzylchloroformate (58 mmoles, 8.25 mL) added dropwise. The resulting solution was stirred at 0° C. for 2 hours, and at ambient temperature for an additional 90 minutes. A white precipitate formed, which was filtered off. Solvent was removed from the filtrate under reduced pressure, and the residue chromatographed on a silica gel column, eluting with 20% ethyl acetate/hexanes, to give benzyl allylcarbamate, a compound of formula (2), as a clear oil. Yield: 5.0 g.

Workup

  1. stirringThe resulting solution was stirred at 0° C. for 2 hours
  2. waitat ambient temperature for an additional 90 minutes
  3. customA white precipitate formed
  4. filtrationwhich was filtered off
  5. customSolvent was removed from the filtrate under reduced pressure
  6. customthe residue chromatographed on a silica gel column
  7. washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-75604d7187b147318690301055b9be17
Source dataset
uspto-grants-2007_04
Patent number
US07205303B2

Reaction notes

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