Acetone → N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-3-methoxy-N-(2-methoxyphenyl)benzamide

HRID 2466

反応式

HRID 2466 の反応式
[CH:1]([CH2:3][N:4]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])[C:5](=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=1)=O.[F:23][C:24]1[CH:37]=[CH:36][C:27]([C:28]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)=[O:29])=[CH:26][CH:25]=1.C([BH3-])#N.[Na+].CC(C)=O>CO.CCOCC>[F:23][C:24]1[CH:25]=[CH:26][C:27]([C:28]([CH:30]2[CH2:35][CH2:34][N:33]([CH2:1][CH2:3][N:4]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[O:21][CH3:22])[C:5](=[O:14])[C:6]3[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[CH:7]=3)[CH2:32][CH2:31]2)=[O:29])=[CH:36][CH:37]=1

参加物

7

反応物 4

HCID 180AcetoneHCID 27244404-(4-Fluorobenzoyl)piperidineHCID 5003444Sodium cyanoborohydrideHCID 19689822N-Formylmethyl-3-methoxy-N-(2-methoxyphenyl)benzamide

生成物 1

HCID 19690003N-{2-[4-(4-Fluorobenzoyl)piperidino]ethyl}-3-methoxy-N-(2-methoxyphenyl)benzamide収率 46.1%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 3283Diethyl Ether溶媒

実験手順

N-Formylmethyl-3-methoxy-N-(2-methoxyphenyl)-benzamide (141 mg, 0.473 mmol), and 4-(4-fluorobenzoyl)piperidine (125 mg, 0.60 mmol) were dissolved in methanol (4.5 ml) to which was subsequently added molecular sieve 4A (300 mg) at room temperature. After 1 hour of stirring at the same temperature, sodium cyanoborohydride (12 mg, 0.191 mmol) was added to the above mixture, followed by 45 minutes of stirring and subsequent addition of acetone (2 ml). The reaction solution was diluted with ether (15 ml) and filtered through cerite, and the solvent was removed by evaporation. The thus obtained colorless oily residue was dissolved in ether (7 ml), mixed with saturated hydrogen chloride/ether solution (7 ml) and stirred for 5 minutes. After removing the ether layer, the reaction solution was mixed with water (7 ml) and potassium carbonate (1.5 g) and extracted with ether and dried on potassium carbonate, and then the solvent was removed by evaporation. Thereafter, the resulting colorless oily residue was purified by subjecting it to a silica gel column chromatography (ether:hexane=3:2) to obtain 107 mg (46.1%) of the title compound in the form of light yellow oil.

後処理

  1. customat room temperature
  2. additionwas added to the above mixture
  3. filtrationfiltered through cerite, and the solvent
  4. customwas removed by evaporation
  5. dissolutionThe thus obtained colorless oily residue was dissolved in ether (7 ml)
  6. additionmixed with saturated hydrogen chloride/ether solution (7 ml)
  7. stirringstirred for 5 minutes
  8. customAfter removing the ether layer
  9. additionthe reaction solution was mixed with water (7 ml) and potassium carbonate (1.5 g)
  10. extractionextracted with ether
  11. customdried on potassium carbonate
  12. customthe solvent was removed by evaporation
  13. customThereafter, the resulting colorless oily residue was purified

出典と根拠

ORDレコード
ord-d8b481bd661041d298e29f0d4a578067
出典データセット
uspto-grants-1998_03
特許番号
US05728835

関連ノート

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