Benzyl chloroformate → HCID 52915464, compound

HRID 400476Notes

Reaction equation

HRID 400476 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([N:19](CCC=C)[CH2:20][CH2:21][CH:22]=[CH2:23])[C:13]1C=CC=[CH:15][CH:14]=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH2:12]([N:19]([CH2:20][CH2:21][CH:22]=[CH2:23])[C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:13][CH:14]=[CH2:15]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 10703903HCID 10703903, compound

Product 1

HCID 52915464HCID 52915464, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

11.2 mL benzylchloroformate was added to 14 g N-benzyl-N-(but-3-enyl)-but-3-en-1-amine in 100 mL toluene at 0° C. After being heated at 70° C. for 3 h, the reaction mixture was cooled to RT, basified with saturated aqueous sodium hydrogencarbonate solution, extracted with ethyl acetate, washed with brine, dried, concentrated, and purified by chromatographie on silica gel (hexane/ethyl acetate 20:1) to yield 16.8 g of the desired product. (M+H)+: 274

Workup

  1. temperaturethe reaction mixture was cooled to RT
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified by chromatographie on silica gel (hexane/ethyl acetate 20:1)

Sources & evidence

ORD record
ord-bdeb7b72b3a14587b5a62375ad46d550
Source dataset
uspto-grants-2014_06
Patent number
US08741892B2

Reaction notes

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