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

HRID 397750Notes

Reaction equation

HRID 397750 reaction equation
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]

Participants

5

Reactant 2

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-1a592814e0464c4cab095ded36bc92e0
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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