p-Toluenesulfonic acid → HCID 18967779、化合物

HRID 399624

反応式

HRID 399624 の反応式
C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:12]1([C:18]([CH:20]2[CH2:22][CH2:21]2)=O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:23]([NH2:26])[CH2:24][CH3:25]>C1(C)C=CC=CC=1>[CH:20]1([CH:18]([NH:26][CH2:23][CH2:24][CH3:25])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:22][CH2:21]1

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 7852PropylamineHCID 77029Cyclopropyl phenyl ketone

生成物 1

HCID 18967779HCID 18967779、化合物

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
55 °C

実験手順

4 Å molecular sieves and 100 mg of paratoluenesulphonic acid are added to 10 g of cyclopropyl phenyl ketone in 60 ml of anhydrous toluene, followed by 6 g of propylamine. Imine formation is monitored by gas chromatographic assay. After heating for 6 hours at 55° C., the reaction mixture is cooled, the molecular sieves are filtered off and the solution is evaporated to dryness under vacuum. The residue is taken up in 100 ml of anhydrous ethanol. The solution is cooled to 0° C. and 2.65 g of sodium borohydride are added portionwise. After stirring overnight at room temperature, the mixture is evaporated to dryness under vacuum and the residue is taken up in water, hydrolysed with 1N hydrochloric acid in order to bring the pH to 2, and washed with ethyl acetate. The pH is brought to 9 by addition of 2N sodium hydroxide and the mixture is then extracted several times with methylene chloride.

後処理

  1. temperaturethe reaction mixture is cooled
  2. filtrationthe molecular sieves are filtered off
  3. customthe solution is evaporated to dryness under vacuum
  4. temperatureThe solution is cooled to 0° C.
  5. addition2.65 g of sodium borohydride are added portionwise
  6. customthe mixture is evaporated to dryness under vacuum
  7. washwashed with ethyl acetate
  8. additionThe pH is brought to 9 by addition of 2N sodium hydroxide
  9. extractionthe mixture is then extracted several times with methylene chloride

出典と根拠

ORDレコード
ord-7bf037825dc44434ac0527981cefa234
出典データセット
uspto-grants-1998_10
特許番号
US05821255

関連ノート

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