Tilorone Hydrochloride → 2,7-Bis(2-diethylaminoethoxy)fluoren-9-ol dihydrochloride

HRID 268517

反応式

HRID 268517 の反応式
[BH4-].[Na+].[ClH:3].Cl.[CH2:5]([N:7]([CH2:33][CH3:34])[CH2:8][CH2:9][O:10][C:11]1[CH:23]=[CH:22][C:21]2[C:20]3[C:15](=[CH:16][C:17]([O:24][CH2:25][CH2:26][N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[CH:18][CH:19]=3)[C:14](=[O:32])[C:13]=2[CH:12]=1)[CH3:6]>CO>[ClH:3].[ClH:3].[CH2:30]([N:27]([CH2:28][CH3:29])[CH2:26][CH2:25][O:24][C:17]1[CH:18]=[CH:19][C:20]2[C:21]3[C:13](=[CH:12][C:11]([O:10][CH2:9][CH2:8][N:7]([CH2:33][CH3:34])[CH2:5][CH3:6])=[CH:23][CH:22]=3)[CH:14]([OH:32])[C:15]=2[CH:16]=1)[CH3:31]

参加物

4

反応物 2

HCID 33958Tilorone HydrochlorideHCID 4311764Sodium borohydride

生成物 1

HCID 215523212,7-Bis(2-diethylaminoethoxy)fluoren-9-ol dihydrochloride

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

A total of 2.3 g (0.06 mole) of sodium borohydride is added in small portions to a stirred solution of 9.7 g (0.02 mole) of 2,7-bis(2-diethylaminoethoxy)fluoren-9-one dihydrochloride in 200 ml or methanol, maintaining the mixture at 0°C throughout the addition. The mixture is allowed to warm to room temperature and the solvent removed in vacuo. The residue is taken up in 10% hydrochloric acid, the mixture extracted with ether, and the aqueous acidic solution evaporated in vacuo. The residue is dissolved in methanol, cooled at -20°C, and the inorganic material which precipitates removed by filtration. The filtrate is evaporated in vacuo, the residue dissolved in water and made basic with 10% aqueous sodium hydroxide. The liberated free base is extracted into ether, the ether extract washed with water and dried over anhydrous magnesium sulfate. The mixture is filtered, the filtrate evaporated, the residue taken up in isopropyl alcohol and acidified to Congo Red with ethereal hydrogen chloride. The precipitated product is collected and recrystallized three times from a mixture of isopropyl alcohol and methanol to give 2,7-bis(2-diethylaminoethoxy)fluoren-9-ol dihydrochloride. M.P. 192°-194°C.

後処理

  1. additionthroughout the addition
  2. temperatureto warm to room temperature
  3. customthe solvent removed in vacuo
  4. extractionthe mixture extracted with ether
  5. customthe aqueous acidic solution evaporated in vacuo
  6. dissolutionThe residue is dissolved in methanol
  7. temperaturecooled at -20°C
  8. customthe inorganic material which precipitates
  9. customremoved by filtration
  10. customThe filtrate is evaporated in vacuo
  11. dissolutionthe residue dissolved in water
  12. extractionThe liberated free base is extracted into ether
  13. extractionthe ether extract
  14. washwashed with water
  15. dry with materialdried over anhydrous magnesium sulfate
  16. filtrationThe mixture is filtered
  17. customthe filtrate evaporated
  18. customThe precipitated product is collected
  19. customrecrystallized three times
  20. additionfrom a mixture of isopropyl alcohol and methanol

出典と根拠

ORDレコード
ord-ec0d74681de04e5ab1bec5ae227697bb
出典データセット
uspto-grants-1976_03
特許番号
US03947593

関連ノート

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