Potassium Hydroxide → 4-(5-Fluoro-2-benzofuranyl)piperidine

HRID 745827ノート

反応式

HRID 745827 の反応式
C(OC([N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:15]=3[CH:16]=2)[CH2:8][CH2:7]1)=O)C.[OH-].[K+]>C(O)CO.C1(C)C=CC=CC=1>[F:21][C:18]1[CH:19]=[CH:20][C:14]2[O:13][C:12]([CH:9]3[CH2:8][CH2:7][NH:6][CH2:11][CH2:10]3)=[CH:16][C:15]=2[CH:17]=1

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 53928071HCID 53928071、化合物

生成物 1

HCID 233123124-(5-Fluoro-2-benzofuranyl)piperidine

試薬・触媒・溶媒 2

HCID 174Ethylene Glycol溶媒HCID 1140Toluene溶媒

実験手順

5.9 g (about 0.02 mole) of 4-(5-fluoro-2-benzofuranyl)-1-piperidinecarboxylic acid ethyl ester is dissolved in 65 ml of ethylene glycol. After the addition of 19.4 g of 86% potassium hydroxide, the cloudy solution formed is heated, with vigorous stirring, for 18 hours at 160°. The reaction solution is thereupon cooled to 100°, diluted with 65 ml of toluene and then cooled to 20°. The organic phases are firstly extracted twice with one liter of water each time, then four times with 200 ml of a 10% solution of methanesulphonic acid in water. The methanesulphonic acid solution is thereupon brought to the pH-value of 12 by the addition of 30% sodium hydroxide solution, and is subsequently extracted with one liter of chloroform. The chloroform solution is dried with sodium sulphate, filtered and concentrated by evaporation to thus obtain crude 4-(5-fluoro-2-benzofuranyl)-piperidine. The base is distilled by molecular distillation in high vacuum. The fraction distilling at 190°-200° and 0.05 Torr is 4-(5-fluoro-2-benzofuranyl)-piperidine. The hydrochloride is prepared with hydrogen chloride in ethyl acetate and recrystallised from ethyl acetate, whereupon it melts at 235°-237°.

後処理

  1. customthe cloudy solution formed
  2. temperatureis heated, with vigorous stirring, for 18 hours at 160°
  3. temperatureThe reaction solution is thereupon cooled to 100°
  4. temperaturecooled to 20°
  5. extractionThe organic phases are firstly extracted twice with one liter of water each time
  6. additionThe methanesulphonic acid solution is thereupon brought to the pH-value of 12 by the addition of 30% sodium hydroxide solution
  7. extractionis subsequently extracted with one liter of chloroform
  8. dry with materialThe chloroform solution is dried with sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated by evaporation

出典と根拠

ORDレコード
ord-36fd44462c544189be5be422f15e1074
出典データセット
uspto-grants-1986_07
特許番号
US04600719

反応ノート

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