Aluminium lithium hydride → N-methyl-N-(8-phenyloctyl)amine

HRID 1743522

反応式

HRID 1743522 の反応式
[CH3:1][NH:2][C:3](=O)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][NH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 22237455N-methyl-8-phenyloctanamide

生成物 1

HCID 22237633N-methyl-N-(8-phenyloctyl)amine収率 83.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of N-methyl-8-phenyloctanamide (25.2 g, 108.0 mmol, 1 eq) in THF (500 mL) cooled to 0° C. was added lithium aluminum hydride (12.3 g, 466.8 mmol, 4.3 eq) portionwise over 20 minutes. The cold bath was removed and the reaction was stirred at rt 3 hours. The reaction was then heated at reflux for 2½ hours. It was then cooled to rt and quenched by the slow addition of H2O (30 mL). EtOAc (300 mL) was added, followed by 2 M NaOH (40 mL). The solids were then filtered off and washed with EtOAc. The filtrate was dried over MgSO4 and concentrated in vacuo to afford N-methyl-N-(8-phenyloctyl)amine (19.7 g, 83%) as a light yellow oil. 1H NMR (CDCl3) δ 7.30–7.14 (m, 5H); 2.63–2.52 (m, 4H); 2.43 (s, 3H); 2.05 (s, 1H); 1.62 (m, 4H); 1.30 (m, 8H).

後処理

  1. customThe cold bath was removed
  2. temperatureThe reaction was then heated
  3. temperatureat reflux for 2½ hours
  4. temperatureIt was then cooled to rt
  5. customquenched by the slow addition of H2O (30 mL)
  6. additionEtOAc (300 mL) was added
  7. filtrationThe solids were then filtered off
  8. washwashed with EtOAc
  9. dry with materialThe filtrate was dried over MgSO4
  10. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-5af0f279327842e08d615e587bb0f1e7
出典データセット
uspto-grants-2006_03
特許番号
US07008636B2

関連ノート

読み込み中…