Potassium Iodide → 4-Methoxy-4-methylpiperidine hydrochloride

HRID 1834513Notes

Reaction equation

HRID 1834513 reaction equation
[Cl:1]CCCC(C1C=CC(F)=CC=1)=O.[CH3:14][C:15]1([O:21][CH3:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.[I-].[K+]>C1(C)C=CC=CC=1>[ClH:1].[CH3:14][C:15]1([O:21][CH3:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 203737104-Methoxy-4-methylpiperidine

Product 1

HCID 203737094-Methoxy-4-methylpiperidine hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 20.1 g (0.1 m) of gamma-chloro-p-fluorobutyrophenone, 30 g (0.2 m) of 4-methyl-4-methoxy-piperidine and 0.1 g. of potassium iodide in 150 ml of toluene is heated in a glass autoclave for 15 hours at 100°-110° C. The KI and the 4-methyl-4-methoxy-piperidine hydrochloride formed in the reaction are separated by filtration and the solvent removed from the filtrate by evaporation under a vacuum on a steam bath. The obtained base is dissolved in ether and the hydrochloride is precipitated with alcoholic HCl. The reaction product is purified by recrystallization from ethanol-ether. Yield 22 g. Melting point 182° C.

Sources & evidence

ORD record
ord-4ab173b5d613407d8003c1e5290fd547
Source dataset
uspto-grants-1978_01
Patent number
US04070473

Reaction notes

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