Sodium Hydroxide → AM-1248

HRID 346447ノート

反応式

HRID 346447 の反応式
[Cl-].C([Al+]CC)C.[C:7]12([C:17](Cl)=[O:18])[CH2:16][CH:11]3[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]3)[CH2:8]1)[CH2:14]2.[CH3:20][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[CH2:27][N:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29]1.[OH-].[Na+]>CCCCCC.C(Cl)Cl>[CH3:20][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH:22]1[CH2:27][N:28]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([C:17]([C:7]23[CH2:16][CH:11]4[CH2:12][CH:13]([CH2:15][CH:9]([CH2:10]4)[CH2:8]2)[CH2:14]3)=[O:18])=[CH:29]1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 989151-Adamantanecarbonyl chlorideHCID 11550392N-(N-Methylpiperidinyl)methylindoleHCID 16686102Diethyl aluminum chloride

生成物 1

HCID 10293794AM-1248

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒3 回HCID 8058Hexane溶媒

実験手順

To the stirring solution of the diethyl aluminum chloride (1.5 ml 1 M soln. in hexane, 180.8 mg, 1.5 mmol) in 10 ml absolute methylene chloride was added at room temp. 298.0 mg (1.5 mmol) 1-adamantanecarbonyl chloride in 5 ml of methylene chloride and the reaction mixture was stirred 15 min. The solution of (N-Methyl-2-piperidinyl)methyl-1H-indole (228.3 mg, 1.0 mmol) in 5 ml of methylene chloride was added during 3 min and mixture was stirred and reflux 48 h. The reaction was work-up by addition of 20 ml 2M solution of sodium hydroxide and extracted by ethyl acetate (3×20 ml), washed to times by water and two times by brine. The combined extract dried by the mixture of sodium sulfate and potassium carbonate. After removing of solvents the rest was purified by chromatography (silica gel, methanol ethyl acetate 1:1).

後処理

  1. temperaturereflux 48 h
  2. extractionextracted by ethyl acetate (3×20 ml)
  3. washwashed to times by water and two times by brine
  4. extractionThe combined extract
  5. dry with materialdried by the mixture of sodium sulfate and potassium carbonate
  6. customAfter removing of solvents the rest
  7. customwas purified by chromatography (silica gel, methanol ethyl acetate 1:1)

出典と根拠

ORDレコード
ord-37550f74ddfb4842819c0a796d16908c
出典データセット
uspto-grants-2007_02
特許番号
US07173027B2

反応ノート

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