Sodium Iodide → HCID 19908333、化合物

HRID 1534807ノート

反応式

HRID 1534807 の反応式
C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].Cl[CH2:10][CH2:11][CH2:12][C:13]1([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[O:17]CCO1.[CH3:24][CH:25]1[CH:30]([C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)[CH2:29][CH:28]([CH3:38])[CH2:27][NH:26]1>CN(C)C=O>[CH:18]1([C:13](=[O:17])[CH2:12][CH2:11][CH2:10][N:26]2[CH2:27][CH:28]([CH3:38])[CH2:29][CH:30]([C:31]3[CH:32]=[CH:33][C:34]([OH:37])=[CH:35][CH:36]=3)[CH:25]2[CH3:24])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 19908331HCID 19908331、化合物HCID 199083322-(3-Chloropropyl)-2-cyclohexyl-1,3-dioxolane

生成物 1

HCID 19908333HCID 19908333、化合物収率 46%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

0.96 g (9 mmol) of sodium carbonate, 1.35 g (9 mmol) of sodium iodide and 2.1 g (9 mmol) of 2-(3-chloropropyl)-2-cyclohexyl-1,3-dioxolane were added to a solution of 1.7 g (8.3 mmol) of 2,5-dimethyl-3-(4-hydroxyphenyl)piperidine in 10 ml of dimethylformamide and the resulting reaction mixture was stirred at a temperature of 80° C. for 16 hours. After cooling, the reaction mixture was poured on ice and extracted three times with ethyl acetate. After evaporating the organic layer under reduced pressure, the residue was dissolved in a mixture of 20 ml of dimethylformamide and 40 ml of 2N hydrochloric acid and stirred for 1 hour so as to split the dioxolane group present. The solution was then extracted three times with diethyl ether, rendered basic by the addition of concentrated ammonia and extracted three times with ethyl acetate. The resulting organic layer was washed three times with water and once with a concentrated saline solution, dried on sodium sulphate an evaporated under reduced pressure. The resulting crude product (2.3 g) was purified by means of flash chromatography over 75 g of silicagel (Merck, grain size 0.040-0.063 mm) using a mixture of dichloromethane, methanol and concentrated ammonia (95:4.5:0.5) as an eluent. After combining and evaporating the desired fractions, totally 1.2 g (46%) of 1-(4-cyclohexyl-4 -oxobutyl)-2,5-dimethyl-3-(4-hydroxyphenyl)piperidine were obtained (compound no. 1).

後処理

  1. customthe resulting reaction mixture
  2. temperatureAfter cooling
  3. additionthe reaction mixture was poured on ice
  4. extractionextracted three times with ethyl acetate
  5. customAfter evaporating the organic layer under reduced pressure
  6. dissolutionthe residue was dissolved in a mixture of 20 ml of dimethylformamide and 40 ml of 2N hydrochloric acid
  7. stirringstirred for 1 hour so as
  8. customto split the dioxolane group present
  9. extractionThe solution was then extracted three times with diethyl ether
  10. additionrendered basic by the addition of concentrated ammonia
  11. extractionextracted three times with ethyl acetate
  12. washThe resulting organic layer was washed three times with water
  13. customonce with a concentrated saline solution, dried on sodium sulphate
  14. customan evaporated under reduced pressure
  15. customThe resulting crude product (2.3 g) was purified by means of flash chromatography over 75 g of silicagel (Merck, grain size 0.040-0.063 mm)
  16. additiona mixture of dichloromethane, methanol and concentrated ammonia (95:4.5:0.5) as an eluent
  17. customevaporating the desired fractions

出典と根拠

ORDレコード
ord-d12de0c103ba461e94ca47bfc6aa1f4a
出典データセット
uspto-grants-1992_02
特許番号
US05091393

反応ノート

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