Water → 2,6-Diphenyl-4-piperidone 1,2-Hexadecylene Ketal

HRID 2254393

反応式

HRID 2254393 の反応式
[C:1]1([CH:7]2[CH2:12][C:11](=[O:13])[CH2:10][CH:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:32]([OH:49])[CH:33](O)[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47].O>C1(C)C=CC=CC=1>[CH2:32]1[O:49][C:11]2([CH2:12][CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[NH:8][CH:9]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:10]2)[O:13][CH:33]1[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]

参加物

6

反応物 4

HCID 962WaterHCID 980371,2-HexadecanediolHCID 521998p-Toluenesulfonic acid monohydrateHCID 28287082,6-Di(phenyl)-4-piperidone

生成物 1

HCID 867471002,6-Diphenyl-4-piperidone 1,2-Hexadecylene Ketal収率 38.6%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 14.6 g (58.0 mmol) of 2,6-diphenyl-4-piperidone and 12.2 g (64 mmol) of p-toluenesulfonic acid monohydrate in 500 mL of toluene is refluxed and the azeotroping water is collected in a Dean Stark trap. When 1 mL of water is collected, 15.0 g (58.0 mmol) of 1,2-hexadecanediol (Aldrich) is added and the reaction is refluxed until another 1 mL of water is collected. The reaction mixture is cooled to room temperature and made basic with 50% aqueous sodium hydroxide solution. The organic layer is separated and the aqueous phase is extracted with toluene (2×100 mL). The combined organic phases are dried over anhydrous magnesium sulfate and the solvent is removed under reduced pressure. 11.0 g (38% yield) of the title compound is isolated after purification by liquid chromatography (LC) (silica gel, ethyl acetate/hexane) followed by recrystallization from ethanol: mp 63°-70° C.

後処理

  1. customthe azeotroping water is collected in a Dean Stark trap
  2. customWhen 1 mL of water is collected
  3. customis collected
  4. customThe organic layer is separated
  5. extractionthe aqueous phase is extracted with toluene (2×100 mL)
  6. dry with materialThe combined organic phases are dried over anhydrous magnesium sulfate
  7. customthe solvent is removed under reduced pressure

出典と根拠

ORDレコード
ord-2febec4c3e434ed3964f3f9c334d127c
出典データセット
uspto-grants-1993_08
特許番号
US05235056

関連ノート

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