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

HRID 2274850노트

반응식

HRID 2274850 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-816e1e940b4146d28113c83a4469ba36
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09126993B2

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