Potassium Carbonate → 1-(2-(4-Chlorophenoxy)ethyl)-4-(4-methylbenzyl)piperidine hydrochloride

HRID 1955228Notes

Reaction equation

HRID 1955228 reaction equation
Cl.[CH3:2][C:3]1[CH:15]=[CH:14][C:6]([CH2:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:5][CH:4]=1.[Cl:16][C:17]1[CH:26]=[CH:25][C:20]([O:21][CH2:22][CH2:23]Br)=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[ClH:16].[Cl:16][C:17]1[CH:26]=[CH:25][C:20]([O:21][CH2:22][CH2:23][N:11]2[CH2:12][CH2:13][CH:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([CH3:2])=[CH:15][CH:14]=3)[CH2:9][CH2:10]2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 748541-(2-Bromoethoxy)-4-chlorobenzeneHCID 232942754-(4-Methylbenzyl)piperidine hydrochloride

Product 1

HCID 232945491-(2-(4-Chlorophenoxy)ethyl)-4-(4-methylbenzyl)piperidine hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared from 4-(4-methylbenzyl)piperidine hydrochloride (600 mg, 2.66 mmol), 2-(4-chlorophenoxy)ethyl bromide (658 mg, 2.79 mmol) and K2CO3 (754 mg, 5.45 mmol) in CH3CN (50 mL) as colorless flakes (661 mg): mp 201-203° C.; 1H NMR (CDCl3) 1.60-2.12 (m, 5H), 2.31 (s, 3H), 2.58 (d, J=7.2 Hz, 2H), 2.63-2.82 (m, 2H), 3.20-3.50 (m, 2H), 3.58-3.70 (m, 2H), 4.53 (t, J=4.2 Hz, 2H), 6.80 (d, J=9.3 Hz, 2H), 7.00 (d, J=7.5 Hz, 2H), 7.09 (d, J=7.8 Hz, 2H), 7.24 (d, J=8.7 Hz, 2H), 12.60 (b, 1H).

Sources & evidence

ORD record
ord-10eccebc9b9941c0804c66974575daca
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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