3-Bromobenzylamine hydrochloride → Benzenemethanamine, 3-bromo-

HRID 1985107Notes

Reaction equation

HRID 1985107 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7]>CC(O)C.C(Cl)Cl.[OH-].[Na+]>[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7]

Participants

5

Reactant 1

HCID 27249803-Bromobenzylamine hydrochloride

Product 1

HCID 457587Benzenemethanamine, 3-bromo-

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideCatalystHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

3-Bromo-benzylamine HCl salt (0.75 g) was dissolved in 10 mL 15% IPA in CH2Cl2. 7 drops of 1ON Sodium Hydroxide (NaOH) was added and stirred for 3 minutes. To the reaction mixture, 5 mL of dH2O was added and stirred for 5 minutes. The IPA/CH2Cl2 layer was extracted. The aqueous layer was rinsed with 10 mL 15% IPA in CH2Cl2. All organic layers were added together and concentrated under vacuum. MS (ESI+) for C7H8BrN m/z 186.3 (M+H)+

Workup

  1. additionTo the reaction mixture, 5 mL of dH2O was added
  2. stirringstirred for 5 minutes
  3. extractionThe IPA/CH2Cl2 layer was extracted
  4. washThe aqueous layer was rinsed with 10 mL 15% IPA in CH2Cl2
  5. additionAll organic layers were added together
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7542dfcbd4e24877b7d21196426e4705
Source dataset
uspto-grants-2009_06
Patent number
US07544717B2

Reaction notes

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