Potassium Iodide → 4-(4-hydroxy-4-(2-(4-hydroxybutyloxy)phenyl)piperidino)-N,N-dimethyl-2,2-diphenylbutaneamide

HRID 279082ノート

反応式

HRID 279082 の反応式
[OH:1][C:2]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[OH:34])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH2:4][CH2:3]1.Br[CH2:36][CH2:37][CH2:38][CH2:39][O:40]C(=O)C.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.C(Cl)(Cl)Cl.O>[OH:1][C:2]1([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[O:34][CH2:36][CH2:37][CH2:38][CH2:39][OH:40])[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])[CH2:4][CH2:3]1

参加物

8

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 784911-Butanol, 4-bromo-, 1-acetateHCID 102263704-[4-(2-hydroxyphenyl)-4-hydroxypiperidin-1-yl]-2,2-diphenyl-N,N-dimethylbutanamide

生成物 1

HCID 102087204-(4-hydroxy-4-(2-(4-hydroxybutyloxy)phenyl)piperidino)-N,N-dimethyl-2,2-diphenylbutaneamide収率 24.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

In 10 mL of anhydrous dimethylformamide was dissolved 920 mg (2 mmol) of 4-(4-hydroxy-4-(2-hydroxyphenyl)piperidino)-N,N-dimethyl-2,2-diphenylbutaneamide. To the resulting solution were added 585 g (3 mmol) of 4-bromobutylacetate, 414 mg (3 mmol) of potassium carbonate and a small amount of potassium iodide. The resulting mixture was stirred under heating at 80° C. for 4 hours. After cooling, the reaction mixture was poured into water, followed by extraction with ethyl acetate, washing with water and drying. The residue obtained by distilling off the solvent under reduced pressure was dissolved in 15 mL of methanol. To the resulting solution was added 3 mL of a 1N aqueous solution of sodium hydroxide, followed by stirring at room temperature for 1 hour. From the reaction mixture, the solvent was distilled off under reduced pressure. The residue thus obtained was dissolved in chloroform. The resulting solution was washed with water and dried. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column, whereby 260 mg (yield: 24.5%) of 4-(4-hydroxy-4-(2-(4-hydroxybutyloxy)phenyl)piperidino)-N,N-dimethyl-2,2-diphenylbutaneamide (Compound No. 34) was obtained.

後処理

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washwashing with water
  4. customdrying
  5. customThe residue obtained
  6. distillationby distilling off the solvent under reduced pressure
  7. dissolutionwas dissolved in 15 mL of methanol
  8. additionTo the resulting solution was added 3 mL of a 1N aqueous solution of sodium hydroxide
  9. stirringby stirring at room temperature for 1 hour
  10. distillationFrom the reaction mixture, the solvent was distilled off under reduced pressure
  11. customThe residue thus obtained
  12. washThe resulting solution was washed with water
  13. customdried
  14. customThe residue obtained
  15. distillationby distilling off the solvent under reduced pressure
  16. customwas purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-162cb439b3c54407abc490dbbad526e4
出典データセット
uspto-grants-2002_03
特許番号
US06362203B1

反応ノート

読み込み中…