p-Xylyl bromide → N,N-diethyl-4-[[4-(4-methylbenzyl)-1-piperazinyl](8-quinolinyl)methyl]benzamide

HRID 1837546Notes

Reaction equation

HRID 1837546 reaction equation
[CH2:1]([N:3]([CH2:29][CH3:30])[C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:27]=2[N:26]=[CH:25][CH:24]=[CH:23]3)[N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH3:2].CCN(CC)CC.[CH3:38][C:39]1[CH:46]=[CH:45][C:42]([CH2:43]Br)=[CH:41][CH:40]=1>C(Cl)Cl>[CH2:29]([N:3]([CH2:1][CH3:2])[C:4](=[O:28])[C:5]1[CH:6]=[CH:7][C:8]([CH:11]([N:12]2[CH2:13][CH2:14][N:15]([CH2:38][C:39]3[CH:46]=[CH:45][C:42]([CH3:43])=[CH:41][CH:40]=3)[CH2:16][CH2:17]2)[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:27]=2[N:26]=[CH:25][CH:24]=[CH:23]3)=[CH:9][CH:10]=1)[CH3:30]

Participants

5

Reactant 3

HCID 7721p-Xylyl bromideHCID 8471TriethylamineHCID 9801260N,N-diethyl-4-(1-piperazinyl(8-quinolinyl)methyl)benzamide

Product 1

HCID 10185707N,N-diethyl-4-[[4-(4-methylbenzyl)-1-piperazinyl](8-quinolinyl)methyl]benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 1 (0.80 g; 1.99 mmol) in CH2Cl2 (20 ml) was added Et3N (0.83 ml; 5.97 mmol) followed by p-methyl benzyl bromide (773 mg; 4.18 mmol). The reaction mixture was stirred overnight and was then was concentrated under reduced pressure. Purification by reverse phase using 10%-30% CH3CN/H2O.

Workup

  1. concentrationwas then was concentrated under reduced pressure
  2. customPurification by reverse phase

Sources & evidence

ORD record
ord-66b7398f7eee44fdb49a148db594eb7b
Source dataset
uspto-grants-2004_08
Patent number
US06784181B2

Reaction notes

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