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

HRID 1926227ノート

反応式

HRID 1926227 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8058Hexane溶媒

反応条件

温度
40 °C

実験手順

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 Two layers formed, but no solid precipitated, even upon cooling, and the hexane layer was withdrawn with a pipette.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).

後処理

  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 customthe hexane layer was withdrawn with a pipette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

出典と根拠

ORDレコード
ord-1ad1fa31ff544cb1ab13354d7531b38f
出典データセット
uspto-grants-2012_05
特許番号
US08178668B2

反応ノート

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