Trifluoroacetic anhydride → 2-(4-Bromo-1-methoxy-naphthalen-2-yl)-1-methylethylamine hydrochloride

HRID 1790297노트

반응식

HRID 1790297 반응식
[ClH:1].[CH3:2][O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][C:5]=1[CH2:14][CH:15]([NH2:17])[CH3:16].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[Br:31]Br>ClCCl>[ClH:1].[Br:31][C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([O:3][CH3:2])=[C:5]([CH2:14][CH:15]([NH2:17])[CH3:16])[CH:6]=1

참가 물질

5

반응물 3

HCID 9845Trifluoroacetic anhydrideHCID 24408BromineHCID 220417522-(1-Methoxy-naphthalen-2-yl)-1-methylethylamine hydrochloride

생성물 1

HCID 220417602-(4-Bromo-1-methoxy-naphthalen-2-yl)-1-methylethylamine hydrochloride

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of the product from Example 4 (1.2 g, 4.78 mmol) and TEA (0.97 g, 9.56 mmol) in dichloromethane (100 ml) at 0° C. was added trifluoroacetic anhydride (1.2 g, 5.74 mmol). The reaction mixture was stirred at 0° C. for 1 h and evaporated to a residue, which was filtered through silica (ethyl acetate/hexane: 2/8). The fractions containing the protected amine were combined and concentrated to a residue that was dissolved in acetic acid (5 mL) and cooled to 0° C. Bromine (0.91 g, 5.74 mmol) was added and the reaction mixture stirred at this temperature for 30 min. The solid that formed was collected by filtration and dissolved in a mixture of methanol in water (1:1, 20 mL). To this solution was added 1 N aqueous sodium hydroxide (3 mL) and the mixture was stirred at room temperature overnight. Volatiles were evaporated and the desired compound was extracted with dichloromethane and transformed to hydrochloride salt, which was recrystallized from methanol-diethyl ether. Analysis. Calcd. for C14H16BrNO.HCl.0.2 CH3OH: C, 65.39; H, 7.21; N, 5.56. Found: C, 65.16; H, 7.07; N, 5.42.

후처리

  1. customevaporated to a residue, which
  2. filtrationwas filtered through silica (ethyl acetate/hexane: 2/8)
  3. additionThe fractions containing the protected amine
  4. concentrationconcentrated to a residue that
  5. dissolutionwas dissolved in acetic acid (5 mL)
  6. temperaturecooled to 0° C
  7. stirringthe reaction mixture stirred at this temperature for 30 min
  8. customThe solid that formed
  9. filtrationwas collected by filtration
  10. dissolutiondissolved in a mixture of methanol in water (1:1, 20 mL)
  11. additionTo this solution was added 1 N aqueous sodium hydroxide (3 mL)
  12. stirringthe mixture was stirred at room temperature overnight
  13. customVolatiles were evaporated
  14. extractionthe desired compound was extracted with dichloromethane
  15. customwas recrystallized from methanol-diethyl ether

출처 및 근거

ORD 기록
ord-322771b3977d4496a9db69836b0f773d
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071225B2

반응 노트

불러오는 중…