Hexylamine → 4-Ethyl-N-hexyl-4-(3-nitrophenyl)piperidine

HRID 397750ノート

反応式

HRID 397750 の反応式
CS(O[CH2:6][CH2:7][C:8]([CH2:25][CH3:26])([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=1)[CH2:9][CH2:10]OS(C)(=O)=O)(=O)=O.[CH2:27]([NH2:33])[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>C1(C)C=CC=CC=1>[NH3:22].[CH2:25]([C:8]1([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)[CH2:7][CH2:6][N:33]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[CH2:10][CH2:9]1)[CH3:26]

参加物

5

反応物 2

HCID 8102HexylamineHCID 230010093-Ethyl-5-((methylsulfonyl)oxy)-3-(3-nitrophenyl)pentyl methanesulfonate

生成物 2

HCID 222AmmoniaHCID 230009754-Ethyl-N-hexyl-4-(3-nitrophenyl)piperidine収率 100.2%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 3-ethyl-5-((methylsulfonyl)oxy)-3-(3-nitrophenyl)pentyl methanesulfonate (Preparation 62, 850 mg, 2.1 mmol) in toluene (6 ml) under an atmosphere of nitrogen was added hexylamine (1.66 ml, 12.6 mmol). The reaction mixture was heated under reflux for 16 h, then it was concentrated in vacuo to give the crude product. This was purified by silica (25 g) column chromatography eluting with ethyl acetate:hexane:0.880 ammonia (49:50:1) to give the title compound as a clear oil (335 mg, 50%).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 16 h
  3. concentrationit was concentrated in vacuo
  4. customto give the crude product
  5. customThis was purified by silica (25 g) column chromatography
  6. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-1a592814e0464c4cab095ded36bc92e0
出典データセット
uspto-grants-2003_08
特許番号
US06610711B2

反応ノート

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