Water → benzyl N-(2-bromoethyl)carbamate

HRID 522699Notes

Reaction equation

HRID 522699 reaction equation
Br.[Br:2][CH2:3][CH2:4][NH2:5].[OH-].[Na+].Cl[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].O>O1CCOCC1>[Br:2][CH2:3][CH2:4][NH:5][C:9](=[O:10])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 27742172-Bromoethylamine hydrobromide

Product 1

HCID 278694benzyl N-(2-bromoethyl)carbamateYield 183%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Treat a 0° C. solution of 2-bromoethylamine hydrobromide (50 g, 0.246 mol) in dioxane (500 mL) with aqueous NaOH (1 M, 492 mL, 0.492 mol), add benzyl chloroformate (21.6 g, 0.127 mol) dropwise, warm to RT and stir overnight. Pour the mixture into H2O, extract with EtOAc (3×), wash the combined organics with brine, dry over Na2SO4, concentrate to dryness and purify via silica gel chromatography (EtOAc/Petroleum ether) to afford the title compound (60 g, 95%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.37-7.33 (m, 5H), 5.12 (s, 2H), 3.61 (t, J=5.6 Hz, 2H), 3.47 (t, J=5.6 Hz, 2H).

Workup

  1. extractionextract with EtOAc (3×)
  2. washwash the combined organics with brine
  3. dry with materialdry over Na2SO4
  4. concentrationconcentrate to dryness
  5. custompurify via silica gel chromatography (EtOAc/Petroleum ether)

Sources & evidence

ORD record
ord-11cc6a834d0347ad8dc275df2013eb3f
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Reaction notes

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