Sodium Hydroxide → 4-Bromobenzylamine

HRID 1814867Notes

Reaction equation

HRID 1814867 reaction equation
Cl.[Br:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[OH-].[Na+]>O>[Br:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 27240964-Bromobenzylamine hydrochloride

Product 1

HCID 775714-Bromobenzylamine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Bromobenzylamine hydrochloride (500 mg) was dissolved in water (25 mL) and 1 M NaOH (2 mL) was added. The mixture was extracted with CH2Cl2 (3×30 mL) and the combined organic layers were concentrated in vacuo to a clear oil. The resulting 4-bromobenzylamine afforded 51 mg of the title compound as a white solid. Physical characteristics. 1H NMR (300 MHz, DMSO-d6) δ 10.54, 8.54, 7.54-7.51, 7.29-7.26, 6.85, 6.36, 6.25, 5.24, 4.68, 4.50, 3.90, 3.75-3.67, 2.77-2.65, 2.28; HRMS (ESI) m/z 514.0994 (M+H)+.

Workup

  1. extractionThe mixture was extracted with CH2Cl2 (3×30 mL)
  2. concentrationthe combined organic layers were concentrated in vacuo to a clear oil

Sources & evidence

ORD record
ord-74ca346066d14d0eb85d527b9be6233b
Source dataset
uspto-grants-2005_04
Patent number
US06878705B2

Reaction notes

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