Piperidine → HCID 20033286, compound

HRID 552122Notes

Reaction equation

HRID 552122 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C(#N)C>[N+:14]([C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][CH:11]=1)[CH2:7][CH2:6][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 219738843-Nitrophenethyl methanesulfonate

Product 1

HCID 20033286HCID 20033286, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 0.49 g (2.0 mmol, 1.0 eq.) of 3-nitrophenethyl methanesulfonate (I-24) and 0.55 g (6.0 mmol, 3.0 eq.) of potassium carbonate in 20 mL of acetonitrile was added 0.4 mL (4.0 mmol, 2.0 eq.) of piperidine. The reaction mixture was stirred at reflux for 16 h. The reaction mixture was allowed to cool to room temperature, filtered and the solvent removed in vacuo. The resulting residue was purified by preparative TLC to provide 0.35 g (1.5 mmol, 75%) of 1-(3-nitrophenethyl)piperidine (I-25).

Workup

  1. temperatureat reflux for 16 h
  2. filtrationfiltered
  3. customthe solvent removed in vacuo
  4. customThe resulting residue was purified by preparative TLC

Sources & evidence

ORD record
ord-96eaee6daa4b4495ac42f339a80fb63b
Source dataset
uspto-grants-2011_05
Patent number
US07951803B2

Reaction notes

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