Ethanol → 4-(3-aminophenyl)-4-ethyl-N-hexylpiperidine

HRID 397751ノート

反応式

HRID 397751 の反応式
[CH2:1]([C:3]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=2)[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:5][CH2:4]1)[CH3:2].C(O)C.[Cl-].[Ca+2].[Cl-]>[Fe].O>[NH3:6].[NH2:21][C:17]1[CH:16]=[C:15]([C:3]2([CH2:1][CH3:2])[CH2:8][CH2:7][N:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14])[CH2:5][CH2:4]2)[CH:20]=[CH:19][CH:18]=1

参加物

7

反応物 3

HCID 702EthanolHCID 5284359Calcium ChlorideHCID 230009754-Ethyl-N-hexyl-4-(3-nitrophenyl)piperidine

生成物 2

HCID 222AmmoniaHCID 230009254-(3-aminophenyl)-4-ethyl-N-hexylpiperidine収率 68%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

実験手順

To a solution of 4-ethyl-N-hexyl-4-(3-nitrophenyl)piperidine (Preparation 63, 335 mg, 1.05 mmol) in 9:1 ethanol:water (41 ml) was added iron powder (530 mg, 9.45 mmol) followed by calcium chloride (58 mg, 0.53 mmol). The reaction mixture was heated under reflux for 2 h, then the mixture was allowed to cool. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was partitioned between dichloromethane (20 ml) and water (20 ml). The phases were separated and the organic extract was dried (MgSO4), filtered and concentrated in vacuo to give the crude product. This was purified by silica (10 g) column chromatography eluting with methanol:dichloromethane:0.880 ammonia (10:89:1) to give the title compound as a brown oil (103 mg, 34%).

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 2 h
  3. temperatureto cool
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customThe residue was partitioned between dichloromethane (20 ml) and water (20 ml)
  7. customThe phases were separated
  8. extractionthe organic extract
  9. dry with materialwas dried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto give the crude product
  13. customThis was purified by silica (10 g) column chromatography
  14. washeluting with methanol

出典と根拠

ORDレコード
ord-0e10e080a9ef46b9b2b56b532859b267
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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