Acetic Acid → 2-(3-Bromophenyl)propan-2-amine hydrochloride

HRID 2274850Notes

Reaction equation

HRID 2274850 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:11]C(=O)C[Cl:14])([CH3:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.C(O)(=O)C>C(O)C>[ClH:14].[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH2:11])([CH3:9])[CH3:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 57593166N-(2-(3-bromophenyl)propan-2-yl)-2-chloroacetamide

Product 1

HCID 532565432-(3-Bromophenyl)propan-2-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of N-(2-(3-bromophenyl)propan-2-yl)-2-chloroacetamide (20.3 g) in ethanol (120 mL) was added acetic acid (20 mL). The reaction mixture was stirred at reflux for 18 h. The solution was cooled to room temperature and the precipitate was filtered off on a celite pad. The filtrate was concentrated and the residue was dissolved in EtOAc. The organic layer was treated with aqueous NaOH [1.0M] solution, dried over Na2SO4 and concentrated. The crude material was treated with a solution of HCl/dioxane [4M]. The intermediate 2-(3-bromophenyl)propan-2-amine hydrochloride was triturated in ether and used as is for the next step (7.50 g, 43%). 1H NMR (400 MHz, CD3OD) δ 7.69 (q, J=1.8 Hz, 1H), 7.55 (ddd, J=1.0, 1.8, 7.9 Hz, 1H), 7.49 (ddd, J=1.0, 2.0, 8.0 Hz, 1H), 7.38 (t, J=8.0 Hz, 1H), 1.71 (s, 6H) ppm.

Workup

  1. temperatureat reflux for 18 h
  2. filtrationthe precipitate was filtered off on a celite pad
  3. concentrationThe filtrate was concentrated
  4. dissolutionthe residue was dissolved in EtOAc
  5. additionThe organic layer was treated with aqueous NaOH [1.0M] solution
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. additionThe crude material was treated with a solution of HCl/dioxane [4M]
  9. customThe intermediate 2-(3-bromophenyl)propan-2-amine hydrochloride was triturated in ether

Sources & evidence

ORD record
ord-816e1e940b4146d28113c83a4469ba36
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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