Water → 1-[3-[4-[(4-Fluorophenyl)(4-methylthien-2-yl)methylene]piperidin-1-ylmethyl]benzoyl]piperidine

HRID 840165ノート

反応式

HRID 840165 の反応式
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:31]2[S:32][CH:33]=[C:34]([CH3:36])[CH:35]=2)=[C:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[CH:20][CH:19]=1.C(N(CC)CC)C.O>C1(C)C=CC=CC=1>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([C:31]2[S:32][CH:33]=[C:34]([CH3:36])[CH:35]=2)=[C:25]2[CH2:30][CH2:29][N:28]([CH2:2][C:3]3[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=3)[C:6]([N:8]3[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]3)=[O:7])[CH2:27][CH2:26]2)=[CH:20][CH:19]=1

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 100144051-[3-(Chloromethyl)benzoyl]piperidineHCID 110770424-[(4-Fluorophenyl)(4-methylthien-2-yl)methylene]piperidine

生成物 1

HCID 99571511-[3-[4-[(4-Fluorophenyl)(4-methylthien-2-yl)methylene]piperidin-1-ylmethyl]benzoyl]piperidine

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of this benzoyl piperidine (2.3 9), the above 4-[(4-fluorophenyl)(4-methylthien-2-yl)methylene]piperidine (3 g) and triethylamine (3 ml) in toluene was boiled under reflux for 5 h. Water was added to the cooled mixture, the layers were separated and the toluene layer was separated, washed with brine, dried over sodium sulphate and evaporated. The resultant oil (5.6 g) was dissolved in dichloromethane and chromatographed on silica. Elution with dichloromethane/ammonium hydroxide (1%) containing increasing amounts of methanol gave fractions that on evaporation gave the title compound (4.36 g). A solution of this compound in ether was treated with with an ethereal solution of hydrogen chloride. The precipitate was collected and dried to give the hydrochloride salt (3.6 g) m.p. 118-142° C.

後処理

  1. temperatureunder reflux for 5 h
  2. customthe layers were separated
  3. customthe toluene layer was separated
  4. washwashed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. dissolutionThe resultant oil (5.6 g) was dissolved in dichloromethane
  8. customchromatographed on silica
  9. washElution with dichloromethane/ammonium hydroxide (1%)
  10. additioncontaining
  11. temperatureincreasing amounts of methanol
  12. customgave fractions that
  13. customon evaporation

出典と根拠

ORDレコード
ord-527ef3e360ce434289e48d02115ab13a
出典データセット
uspto-grants-2002_04
特許番号
US06365604B1

反応ノート

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