1-Iodopropane → N-propyl-3-(m-trifluoromethylphenyl)-piperidine

HRID 128219Notes

Reaction equation

HRID 128219 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.[CH2:17](I)[CH2:18][CH3:19]>CC(C)=O.[Ag]=O>[CH2:17]([N:11]1[CH2:12][CH2:13][CH2:14][CH:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:4]=2)[CH2:10]1)[CH2:18][CH3:19]

Participants

5

Reactant 2

HCID 336431-IodopropaneHCID 30490313-[3-(Trifluoromethyl)phenyl]piperidine

Product 1

HCID 3053803N-propyl-3-(m-trifluoromethylphenyl)-piperidine

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 180AcetoneSolvent

Procedure

A mixture of 4.6 g of the product of Step A in 25 ml of acetone was stirred until dissolution occured and then 2.5 g of silver oxide were added thereto. The mixture was cooled on an ice bath and 2.5 ml of propyl iodide were added dropwise over 5 minutes. The temperature went back to room temperature and the mixture was stirred for 16 hours and was filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with a 85-10-5 cyclohexane-chloroform-triethylamine mixture and evaporation to dryness under reduced pressure yielded 4.3 g of N-propyl-3-(m-trifluoromethylphenyl)-piperidine.

Workup

  1. temperatureThe mixture was cooled on an ice bath
  2. customwent back to room temperature
  3. stirringthe mixture was stirred for 16 hours
  4. filtrationwas filtered
  5. customThe filtrate was evaporated to dryness under reduced pressure
  6. customthe residue was chromatographed over silica gel
  7. washElution
  8. customwith a 85-10-5 cyclohexane-chloroform-triethylamine mixture and evaporation to dryness under reduced pressure

Sources & evidence

ORD record
ord-ddc013fbb57a48b1a72865c60111461e
Source dataset
uspto-grants-1981_03
Patent number
US04259337

Reaction notes

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