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

HRID 484831Notes

Reaction equation

HRID 484831 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 then the solution was separated into the diethyl ether solution and 20% aqueous sodium hydroxide solution. After the ether layer was dried over 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 developing solvent to give 5.46 g of 1-(1-methyl-3-phenoxypropyl)piperidine in a yield of 75%.

Workup

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

Sources & evidence

ORD record
ord-60be75fe60f94abda7ab5e3317ecab52
Source dataset
uspto-grants-1985_08
Patent number
US04533731

Reaction notes

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