Tert-Butylamine → 1-tert-Butyl-4-piperidone

HRID 394095

反応式

HRID 394095 の反応式
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].[I-].C([N+]1(C)[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)C.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.O>[C:1]([N:5]1[CH2:14][CH2:13][C:12](=[O:15])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

参加物

6

反応物 3

HCID 6385Tert-ButylamineHCID 516892Sodium BicarbonateHCID 110975681-Ethyl-1-methyl-4-oxopiperidin-1-ium iodide

生成物 1

HCID 738401-tert-Butyl-4-piperidone

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
78 °C

実験手順

To a solution of 137 mL (1.3 moles) of tert-butylamine in 700 mL of toluene was added solution of 70 g (0.260 moles) of 1-ethyl-1-methyl-4-oxopiperidinium iodide and 2.18 g (0.026 moles) of NaHCO3 in 100 mL of water. The mixture was stirred at 78° C. for 6 h. After it had cooled to rt, the layers were separated and the aq layer was washed with three 200 mL portions of ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), and concentrated to an oil that purified by distillation under reduced pressure. Fractions distilling at 72° C. at 3 mm were collected to afford the title compound as a colorless liquid. 1H NM(CDCl3, 500 MHz): δ 1.15 (s, 9H), 2.45 (t, 4H, J=6.1 Hz), 2.86 (t, 4H, J=6.1H); Mass spectrum (ESI) 156 (M+1).

後処理

  1. temperatureAfter it had cooled to rt
  2. customthe layers were separated
  3. washthe aq layer was washed with three 200 mL portions of ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to an oil
  7. distillationthat purified by distillation under reduced pressure
  8. distillationFractions distilling at 72° C. at 3 mm
  9. customwere collected

出典と根拠

ORDレコード
ord-375eb11d20fd412ca3859f1fc127a98e
出典データセット
uspto-grants-2004_10
特許番号
US06809199B2

関連ノート

読み込み中…