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

HRID 397751Notes

Reaction equation

HRID 397751 reaction equation
[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

Participants

7

Reactant 3

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

Product 2

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

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-0e10e080a9ef46b9b2b56b532859b267
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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