Water → 4-(4-Methylphenyl)-1-methyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine

HRID 2072814

反応式

HRID 2072814 の反応式
[H-].[Na+].[OH:3][C:4]1([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)[CH2:9][CH2:8][N:7]([CH3:10])[CH2:6][CH2:5]1.[F:18][C:19]1[C:24](F)=[C:23]([F:26])[C:22]([F:27])=[C:21]([F:28])[C:20]=1[F:29].O>CN(C)C=O>[CH3:17][C:14]1[CH:13]=[CH:12][C:11]([C:4]2([O:3][C:24]3[C:23]([F:26])=[C:22]([F:27])[C:21]([F:28])=[C:20]([F:29])[C:19]=3[F:18])[CH2:9][CH2:8][N:7]([CH3:10])[CH2:6][CH2:5]2)=[CH:16][CH:15]=1

参加物

6

反応物 4

HCID 962WaterHCID 9805HexafluorobenzeneHCID 24758Sodium hydrideHCID 148370371-Methyl-4-(4-methylphenyl)piperidin-4-OL

生成物 1

HCID 148370634-(4-Methylphenyl)-1-methyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒3 回

反応条件

温度
85 °C

実験手順

To a suspension of sodium hydride (2.2 g, 60% in oil) in 20 ml of dimethylformamide, was added a solution of 11.0 g of 4-hydroxy-4-(4-methylphenyl)-1-methylpiperidine in 50 ml of dimethylformamide. After heating to 85° C. for thirty minutes, the mixture was cooled with an ice-bath, and treated over a period of ten minutes with a solution of 7 ml of hexafluorobenzene in 20 ml of dimethylformamide. After stirring at ambient temperature for twenty hours, the mixture was poured into 200 ml water, stirred for five minutes, then extracted with ethyl acetate (2×). The organic layer was washed with water (2×), followed by a saturated solution of sodium chloride, and dried over anhydrous magnesium sulfate. After filtering, evaporation of the solvent afforded a residue which was purified by means of high pressure liquid chromatography (silica gel; elution with 10% methanol/dichlormethane). The desired fractions were combined, and evaporated to yield 13 g of (4-(4-methylphenyl)-1-methyl-4-(2,3,4,5,6-pentafluorophenoxy) piperidine as an oil.

後処理

  1. temperaturethe mixture was cooled with an ice-bath
  2. stirringstirred for five minutes
  3. extractionextracted with ethyl acetate (2×)
  4. washThe organic layer was washed with water (2×)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtering
  7. customevaporation of the solvent
  8. customafforded a residue which
  9. customwas purified by means of high pressure liquid chromatography (silica gel; elution with 10% methanol/dichlormethane)
  10. customevaporated

出典と根拠

ORDレコード
ord-b02a2d5f4e6740f49d43218d4745d124
出典データセット
uspto-grants-1990_04
特許番号
US04914204

関連ノート

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