1-Phenethylamine → 2,2-Dimethoxy-N-(1-phenylethyl)acetamide

HRID 1926227노트

반응식

HRID 1926227 반응식
[CH3:1][O:2][CH:3]([O:8][CH3:9])[C:4](OC)=[O:5].[CH3:10][CH:11]([NH2:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCCCCC>[CH3:1][O:2][CH:3]([O:8][CH3:9])[C:4]([NH:18][CH:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:10])=[O:5]

참가 물질

4

반응물 2

HCID 74081-PhenethylamineHCID 66647Acetic acid, 2,2-dimethoxy-, methyl ester

생성물 1

HCID 214193672,2-Dimethoxy-N-(1-phenylethyl)acetamide

시약·촉매·용매 1

HCID 8058Hexane용매

반응 조건

온도
40 °C

실험 절차

A mixture of methyl dimethoxyacetate (2.10 g, 15.6 mmol) and α-methylbenzylamine (1.90 g, 15.7 mmol) was stirred at ambient temperature for 5 d and at 40° C. for 4 d. To the reaction mixture was added hexane (5 mL), and the mixture was sonicated. Two layers formed, but no solid precipitated, even upon cooling, and the hexane layer was withdrawn with a pipette. This was repeated twice. The residue was dissolved in EtOAc (≈100 mL), and the solution was washed with aqueous solutions of NH4Cl, NaHCO3, and brine, and dried over MgSO4. The solution was filtered and dried in vacuo overnight to give the title compound as pale yellow oil. 1H NMR (CDCl3, 400 MHz): δ=7.38-7.30 (m, 4H), 7.29-7.24 (m, 1H), 6.80 (brs, 1H), 5.16 (dq, J=8.0, 6.8 Hz, 1H), 4.70 (s, 1H), 3.42 (s, 3H), 3.36 (s, 3H), 1.52 (d, J=6.8 Hz, 3H). MS(ES+): m/z=246.07 (64) [MNa+], 224.11 (78) [MH+], 192.11 (52) [MH+-MeOH], 160.10 (60) [MH+-2 MeOH]. HPLC: tR=2.76 min (polar—5 min, ZQ3).

후처리

  1. customthe mixture was sonicated
  2. customTwo layers formed
  3. customno solid precipitated
  4. temperatureeven upon cooling
  5. customthe hexane layer was withdrawn with a pipette
  6. dissolutionThe residue was dissolved in EtOAc (≈100 mL)
  7. washthe solution was washed with aqueous solutions of NH4Cl, NaHCO3, and brine
  8. dry with materialdried over MgSO4
  9. filtrationThe solution was filtered
  10. customdried in vacuo overnight

출처 및 근거

ORD 기록
ord-1ad1fa31ff544cb1ab13354d7531b38f
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178668B2

반응 노트

불러오는 중…