Diethyl Ether → 1-(1-Methyl-3-phenoxypropyl)piperidine

HRID 1632301Notes

Reaction equation

HRID 1632301 reaction equation
S(C1C=CC(C)=CC=1)(O[CH:5]([CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:6])(=O)=O.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C(OCC)C.C(Cl)(Cl)Cl>CO>[CH3:6][CH:5]([N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[CH2:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6212ChloroformHCID 8082PiperidineHCID 133267624-Phenoxy-2-butyl tosylate

Product 1

HCID 201358121-(1-Methyl-3-phenoxypropyl)piperidineYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a sealed tube, 10 g of the 4-phenoxy-2-butyl tosylate was reacted with 11.2 g of piperidine in 60 ml of absolute methyl alcohol for one hour at 125° C. After the reaction solution was condensed under reduced pressure. 100 ml of diethyl ether was added into the solution and the solution was separated with 20% aqueous sodium hydroxide solution. After the ether layer was dried with anhydrous sodium sulfate, ether was removed under reduced pressure therefrom. The residue thus obtained was subjected to an alumina-column chromatography using chloroform as the solvent to give 5.46 g of 1-(1-methyl-3-phenoxypropyl)piperidine in a yield of 75%.

Workup

  1. customcondensed under reduced pressure
  2. customthe solution was separated with 20% aqueous sodium hydroxide solution
  3. dry with materialAfter the ether layer was dried with anhydrous sodium sulfate, ether
  4. customwas removed under reduced pressure
  5. customThe residue thus obtained

Sources & evidence

ORD record
ord-2000e48365a54d3d878fbdde4f6d8979
Source dataset
uspto-grants-1984_10
Patent number
US04474964

Reaction notes

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