Hydrochloric Acid → HCID 61401039, compound

HRID 1755008Notes

Reaction equation

HRID 1755008 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3].Cl.[Br:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1.N1C=CC=CC=1.Cl>CN(C=O)C>[CH2:5]([O:4][C:2](=[O:3])[NH:16][CH2:15][C:14]1[CH:17]=[CH:18][C:11]([Br:10])=[CH:12][CH:13]=1)[CH:6]([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 62365Isobutyl chloroformateHCID 27240964-Bromobenzylamine hydrochloride

Product 1

HCID 61401039HCID 61401039, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Isobutyl chloroformate (0.152 ml, 1.17 mmol) was added to a solution of 4-bromo-benzylamine hydrochloride (200 mg, 0.899 mmol) and pyridine (0.182 ml, 2.25 mmol) in DMF (2.0 ml), and the mixture was stirred at room temperature for 1.5 hours. A 1 N aqueous HCl solution was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was sequentially washed with water and saturated brine and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate) to give (4-bromo-benzyl)-carbamic acid isobutyl ester (180 mg, 70%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was sequentially washed with water and saturated brine
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (dichloromethane-ethyl acetate)

Sources & evidence

ORD record
ord-c574ffd0e0824f3490aeec0f28603043
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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