Sodium Hydroxide → 9H-Xanthen-9-one, 3,6-bis(2-(piperidino)ethoxy)-

HRID 441638

反応式

HRID 441638 の反応式
O[C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12](O[C:14]=2[CH:15]=1)=[CH:11][C:10]([OH:16])=[CH:9][CH:8]=3.[CH3:18][O-:19].[Na+].[N:21]1([CH2:27][CH2:28]Cl)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[OH-:30].[Na+]>C(O)C.C(Cl)(Cl)Cl.O.ClC1C=CC=CC=1.CO>[N:21]1([CH2:27][CH2:18][O:19][C:2]2[CH:3]=[CH:4][C:5]3[C:6](=[O:17])[C:7]4[C:12]([O:30][C:14]=3[CH:15]=2)=[CH:11][C:10]([O:16][CH2:28][CH2:27][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:9][CH:8]=4)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

参加物

10

反応物 4

HCID 14798Sodium HydroxideHCID 748271-(2-Chloroethyl)piperidineHCID 57493223,6-dihydroxy-9H-xanthen-9-oneHCID 10942334Sodium Methoxide

生成物 1

HCID 2170179H-Xanthen-9-one, 3,6-bis(2-(piperidino)ethoxy)-

試薬・触媒・溶媒 5

HCID 702Ethanol溶媒HCID 887Methanol溶媒HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 7964Chlorobenzene溶媒

実験手順

To 54.5 g (0.239 mole) of 3,6-dihydroxyxanthen-9-one is added 240 ml of methanol and 29.0 g (0.717 mole) of sodium methoxide with stirring after which 700 ml of chlorobenzene is added. Methanol is distilled off until the reaction temperature reaches 130° C. After cooling the reaction mixture to less than about 100° C., 74.5 g (0.5 mole) of 2-piperidinoethylchloride is added and the reaction mixture refluxed for 41/2 hours followed by the addition of 600 ml of water and 20 ml of 50% NaOH with stirring continued for 1/2 hour. The mixture is cooled and chloroform is added to completely dissolve the product. The chlorobenzene-chloroform layer is separated and the aqueous layer is extracted into chloroform. The combined organic layers are washed with water, dried over anhydrous magnesium sulfate and evaporated to give a dark brown oil which solidified upon cooling. The solid is dissolved in boiling ethanol, precipitated with water, cooled and filtered. The resulting solid is dried in vacuo and recrystallized from hexane to give 3,6-bis(2-piperidinoethoxy)xanthone, M.P. 134°-134.5° C.

後処理

  1. additionis added
  2. distillationMethanol is distilled off until the reaction temperature
  3. customreaches 130° C
  4. temperatureAfter cooling the reaction mixture to less than about 100° C.
  5. temperaturethe reaction mixture refluxed for 41/2 hours
  6. temperatureThe mixture is cooled
  7. dissolutionto completely dissolve the product
  8. customThe chlorobenzene-chloroform layer is separated
  9. extractionthe aqueous layer is extracted into chloroform
  10. washThe combined organic layers are washed with water
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customevaporated
  13. customto give a dark brown oil which
  14. temperatureupon cooling
  15. dissolutionThe solid is dissolved
  16. customprecipitated with water
  17. temperaturecooled
  18. filtrationfiltered
  19. customThe resulting solid is dried in vacuo
  20. customrecrystallized from hexane

出典と根拠

ORDレコード
ord-ba349b885d9b418f88d3ae2b7a212b0f
出典データセット
uspto-grants-1977_08
特許番号
US04041165

関連ノート

読み込み中…