Benzyl chloroformate → Benzyl 3-bromopropylcarbamate

HRID 339727

Reaction equation

HRID 339727 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.Br.[Br:13][CH2:14][CH2:15][CH2:16][NH2:17]>C(Cl)Cl.[OH-].[Na+]>[Br:13][CH2:14][CH2:15][CH2:16][NH:17][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 10387Benzyl chloroformateHCID 787013-Bromopropylamine hydrobromide

Product 1

HCID 254436Benzyl 3-bromopropylcarbamateYield 105.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Benzylchloroformate (8.6 ml, 60 mmol) was added to a stirred mixture of 3-bromopropylamine hydrobromide (6.6 g, 30 mmol) in methylene chloride (100 ml) and 3N sodium hydroxide solution (100 ml) at 0° C. After stirring two phase reaction mixture at room temperature for overnight, organic layer was separated and washed with water twice (30 ml×2). After drying with MgSO4, the volatile solvent was evaporated under reduced pressure. The residue was purified with silica gel column chromatography (EtOAc:Hx=1:4) to obtain desire compound (8.6 g, 98%) as colorless oil.

Workup

  1. customtwo phase reaction mixture at room temperature for overnight
  2. customorganic layer was separated
  3. washwashed with water twice (30 ml×2)
  4. dry with materialAfter drying with MgSO4
  5. customthe volatile solvent was evaporated under reduced pressure
  6. customThe residue was purified with silica gel column chromatography (EtOAc:Hx=1:4)

Sources & evidence

ORD record
ord-8d5f0cc8a2fd49aa9f4c3dc927ecccc8
Source dataset
uspto-grants-2014_11
Patent number
US08895558B2

Linked notes

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