Benzyl chloroformate → Benzyl prop-2-yn-1-ylcarbamate

HRID 890807Notes

Reaction equation

HRID 890807 reaction equation
[CH2:1]([NH2:4])[C:2]#[CH:3].[CH2:5]([O:12][C:13](Cl)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>N1C=CC=CC=1.C(Cl)Cl>[CH2:5]([O:12][C:13](=[O:14])[NH:4][CH2:1][C:2]#[CH:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 239041Propargylamine

Product 1

HCID 11137906Benzyl prop-2-yn-1-ylcarbamateYield 32.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of propargylamine (6.4 g, 71.2 mmol) in pyridine (100 mL) was added benzylchloroformate (13.37 g, 78.2 mmol) in 100 mL CH2Cl2 over 0.5 h. The reaction was stirred for 16 h and the volatiles were removed in vacuo. The residue was dissolved in EtOAc and the organic solution was washed with water (2×). The organic solution was washed with dilute aqueous HCl followed by saturated NaHCO3. The organic solution was dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound (4.43 g).

Workup

  1. customthe volatiles were removed in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washthe organic solution was washed with water (2×)
  4. washThe organic solution was washed with dilute aqueous HCl
  5. dry with materialThe organic solution was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-334d5501e1834bd8a8ade45f45f454a3
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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