4-Chlorophenol → 1-Methyl-2-(2-p-chlorophenoxyethyl)-piperidine

HRID 28122

Reaction equation

HRID 28122 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH3:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[CH2:18][CH2:19]Cl>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.C(Cl)Cl>[CH3:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[CH2:18][CH2:19][O:10][C:7]1[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 46844-ChlorophenolHCID 14798Sodium HydroxideHCID 30165662-(2-Chloroethyl)-1-methylpiperidine

Product 1

HCID 233391731-Methyl-2-(2-p-chlorophenoxyethyl)-piperidine

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

200 ml of 50% aqueous sodium hydroxide solution and 1 g of triethylbenzylammonium chloride are added to a solution of 12.8 g of p-chlorophenol in 100 ml of CH2Cl2 ; 16.2 g of 1-methyl-2-(2-chloroethyl)-piperidine are added dropwise, while stirring; and the reaction mixture is stirred for a further one hour. After customary working up, 1-methyl-2-(2-p-chlorophenoxyethyl)-piperidine is obtained. Hydrochloride, m.p. 139°-140°.

Workup

  1. stirringand the reaction mixture is stirred for a further one hour

Sources & evidence

ORD record
ord-2812348ef1c64c43accd809c79458783
Source dataset
uspto-grants-1980_09
Patent number
US04225608

Linked notes

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