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

HRID 2223734Notes

Reaction equation

HRID 2223734 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 aqueous KHSO4 (50 mL) and brine (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 aqueous KHSO4 (50 mL) and brine (50 mL)
  3. dry with materialthe organic phase is dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-631fc1964fdf4380b5d012b9551c5490
Source dataset
uspto-grants-2008_05
Patent number
US07375227B2

Reaction notes

Loading…