Potassium Carbonate → 3,5-Dimethyl-1-(3-Methyl-4-Nitrobenzyl)piperidine

HRID 1500174ノート

反応式

HRID 1500174 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:5]Br.[CH3:13][CH:14]1[CH2:19][CH:18]([CH3:20])[CH2:17][NH:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:13][CH:14]1[CH2:19][CH:18]([CH3:20])[CH2:17][N:16]([CH2:5][C:4]2[CH:7]=[CH:8][C:9]([N+:10]([O-:12])=[O:11])=[C:2]([CH3:1])[CH:3]=2)[CH2:15]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 1182593,5-DimethylpiperidineHCID 44459783-Methyl-4-nitrobenzyl bromide

生成物 1

HCID 533585523,5-Dimethyl-1-(3-Methyl-4-Nitrobenzyl)piperidine収率 61%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

3-Methyl-4-nitrobenzyl bromide (1.00 g), 3,5-dimethylpiperidine (0.60 ml) and potassium carbonate (0.90 g) were dissolved in acetone (20 ml), followed by heating under reflux for 6 hours. The reaction solution was concentrated under reduced pressure, dissolved in chloroform (10 ml), poured into water (100 ml) and extracted with chloroform (50 ml). The organic layer was washed with saturated brine (100 ml), dried over anhydrous sodium sulfate and, after filtration, concentrated under reduced pressure. The residue was purified by silica gel flash column chromatography (developing solvent: n-hexane/ethyl acetate=10:1) to obtain the subject compound (NCR-7) (0.70 g, yield 61%) as a yellow oil.

後処理

  1. temperatureby heating
  2. temperatureunder reflux for 6 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. dissolutiondissolved in chloroform (10 ml)
  5. additionpoured into water (100 ml)
  6. extractionextracted with chloroform (50 ml)
  7. washThe organic layer was washed with saturated brine (100 ml)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationafter filtration
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was purified by silica gel flash column chromatography (developing solvent: n-hexane/ethyl acetate=10:1)
  12. customto obtain the subject compound (NCR-7) (0.70 g, yield 61%) as a yellow oil

出典と根拠

ORDレコード
ord-2b9d2d25a2154c028c5f4e8e61c44dbe
出典データセット
uspto-grants-2015_12
特許番号
US09206125B2

反応ノート

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