Benzyl succinimido carbonate → benzyl N-(2-bromoethyl)carbamate

HRID 2354055Notes

Reaction equation

HRID 2354055 reaction equation
Br.[Br:2][CH2:3][CH2:4][NH2:5].[CH2:6]([O:13][C:14](ON1C(=O)CCC1=O)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(Cl)Cl>[CH2:6]([O:13][C:14](=[O:15])[NH:5][CH2:4][CH2:3][Br:2])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 83172Benzyl succinimido carbonateHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 278694benzyl N-(2-bromoethyl)carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Bromoethylamine hydrobromide (15 g, 73 mmol) and N-(benzyloxycarbonyloxy)-succinimide (15.5 g, 62 mmol) are suspended in CH2Cl2 (150 mL) at 0° C. TEA (9 mL, 65 mmol) is added slowly keeping the temperature at 0° C. After 1 h the mixture is washed with 0.5M aq. KHSO4 (50 mL) and sat. aq. NaCl (50 mL), the organic phase is dried (Na2SO4), filtered and evaporated to provide the title compound.

Workup

  1. customat 0° C
  2. washAfter 1 h the mixture is washed with 0.5M aq. KHSO4 (50 mL) and sat. aq. NaCl (50 mL)
  3. dry with materialthe organic phase is dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-b3a823c92c5b47b2b219f541aec75de2
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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