Benzyl chloroformate → HCID 52915464, compound

HRID 239173Notes

Reaction equation

HRID 239173 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-bac65464023247eabfab48dad31d2ae1
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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