Propargyl bromide → 4-Tert-butyl-1-(prop-2-ynyl)piperidine

HRID 67924

反応式

HRID 67924 の反応式
C(=O)([O-])[O-].[K+].[K+].[C:7]([CH:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)([CH3:10])([CH3:9])[CH3:8].Br[CH2:18][C:19]#[CH:20]>CC(C)=O>[C:7]([CH:11]1[CH2:16][CH2:15][N:14]([CH2:20][C:19]#[CH:18])[CH2:13][CH2:12]1)([CH3:10])([CH3:9])[CH3:8]

参加物

5

反応物 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 74661Piperidine, 4-(1,1-dimethylethyl)-

生成物 1

HCID 127998624-Tert-butyl-1-(prop-2-ynyl)piperidine収率 83.6%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

反応条件

温度
0 °C

実験手順

Anhydrous potassium carbonate (196 g) was added to a solution of 4-tert-butylpiperidine (98.9 g) in anhydrous acetone (1.2 liters) and the resulting suspension was cooled to 0° C., with stirring under an inert atmosphere. A solution of 1-bromoprop-2-yne (87.5 g) in anhydrous acetone (100 ml) was then added dropwise, the temperature being maintained below 5° C. The reaction mixture was then stirred at ambient temperature for 24 hours, filtered and the filtrate was evaporated under reduced pressure (water-pump). The residual oil thus obtained was extracted with petroleum spirit (b.p. 40°-60° C.). The resulting solution was treated with decolourizing charcoal, filtered and the filtrate was evaporated to give 4-tert-butyl-1-(prop-2-ynyl)piperidine (105 g), m.p. 48°-49° C., which may be further purified by distillation under reduced pressure (water-pump) (b.p. 108°-110° C./15 mm Hg) or by sublimation under reduced pressure (water-pump) at 80° C./20 mm Hg.

後処理

  1. temperaturethe temperature being maintained below 5° C
  2. stirringThe reaction mixture was then stirred at ambient temperature for 24 hours
  3. filtrationfiltered
  4. customthe filtrate was evaporated under reduced pressure (water-pump)
  5. customThe residual oil thus obtained
  6. extractionwas extracted with petroleum spirit (b.p. 40°-60° C.)
  7. additionThe resulting solution was treated with decolourizing charcoal
  8. filtrationfiltered
  9. customthe filtrate was evaporated

出典と根拠

ORDレコード
ord-00ba3398f7a04217844c08dec1bb7d5d
出典データセット
uspto-grants-1982_08
特許番号
US04347252

関連ノート

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