Benzyl chloroformate → Benzyl 3-bromopropylcarbamate

HRID 2256394Notes

Reaction equation

HRID 2256394 reaction equation
Br.[Br:2][CH2:3][CH2:4][CH2:5][NH2:6].[CH2:7]([O:14][C:15](Cl)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>[C:15]([NH:6][CH2:5][CH2:4][CH2:3][Br:2])([O:14][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:16]

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 787013-Bromopropylamine hydrobromide

Product 1

HCID 254436Benzyl 3-bromopropylcarbamateYield 79%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolvent

Procedure

To a stirred solution of 1-bromo-3-propylamine hydrobromide (5 g, 22.84 mmol) in saturated aqueous sodium carbonate (100 mL) and ethyl acetate (200 mL) at 0° C., was added benzylchloroformate (3.2 mL, 22.84 mmol) and the resulting mixture was warmed to room temperature and stirred overnight. The aqueous layer was separated and extracted with ethyl acetate (2×100 mL) and the combined organic layers were washed with brine (2×100 mL), dried over sodium sulfate and evaporated to dryness under reduced pressure. Silica gel chromatography using ethyl acetate/hexanes (1:9) provided the title compound as a colorless oil (4.7 g, 79%).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with ethyl acetate (2×100 mL)
  3. washthe combined organic layers were washed with brine (2×100 mL)
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-4312125b14f3453187ea421af213d97c
Source dataset
uspto-grants-1997_08
Patent number
US05654431

Reaction notes

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