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1,1'-(4-Chlorobutylidene)bis(4-fluorobenzene) → 1-[4,4-Bis-(4-fluorophenyl)butyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine

HRID 2072810
ノート
印刷プレビュー

反応式

HRID 2072810 の反応式
C(=O)(O)[O-].[Na+].[F:6][C:7]1[C:19]([F:20])=[C:18]([F:21])[C:17]([F:22])=[C:16]([F:23])[C:8]=1[O:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.[F:24][C:25]1[CH:30]=[CH:29][C:28]([CH:31]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)[CH2:32][CH2:33][CH2:34]Cl)=[CH:27][CH:26]=1>CN(C)C=O>[F:24][C:25]1[CH:26]=[CH:27][C:28]([CH:31]([C:36]2[CH:37]=[CH:38][C:39]([F:42])=[CH:40][CH:41]=2)[CH2:32][CH2:33][CH2:34][N:13]2[CH2:14][CH2:15][CH:10]([O:9][C:8]3[C:16]([F:23])=[C:17]([F:22])[C:18]([F:21])=[C:19]([F:20])[C:7]=3[F:6])[CH2:11][CH2:12]2)=[CH:29][CH:30]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 516892Sodium BicarbonateHCID 148370404-(2,3,4,5,6-Pentafluorophenoxy)piperidine

生成物 1

HCID 148370581-[4,4-Bis-(4-fluorophenyl)butyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
78 °C

実験手順

A stirring mixture of 10 g of sodium bicarbonate in 50 ml dimethylformamide was treated with 4.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine followed by a solution of 4.06 ml of 4,4-bis-(4-fluorophenyl)butyl chloride in 10 ml of dimethylformamide, and then stirred at 78° C. for 20 hours. After filtering, the filtrate was poured into water and extracted with ethyl acetate. The organic layer was washed with water followed by a saturated sodium chloride solution and dried over anhydrous magnesium sulfate. Filtration followed by evaporation of the volatiles afforded a residue which was purified by means of high pressure liquid chromatography (silica gel; elution with 20% ethyl acetate/dichloromethane) to afford 5.44 g of 1-[4,4-bis-(4-fluorophenyl)butyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine as an oil. The oil was dissolved in hot isopropanol and acidified with an etheral solution of oxalic acid to precipitate the corresponding oxalate salt. Recrystallization from isopropanol afforded 2.75 g (30.0%) of 1-[4,4-bis-(4-fluorophenyl)butyl]-4-(2,3,4,5,6-pentafluorophenoxy)piperidine oxalate, m.p. 182°-185° C.

後処理

  1. filtrationAfter filtering
  2. additionthe filtrate was poured into water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationFiltration
  7. customfollowed by evaporation of the volatiles
  8. customafforded a residue which
  9. customwas purified by means of high pressure liquid chromatography (silica gel; elution with 20% ethyl acetate/dichloromethane)

出典と根拠

ORDレコード
ord-ed65700e08fb4e1f8bbe26e168618855
出典データセット
uspto-grants-1990_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04914204

反応ノート

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