Potassium Carbonate → N1-phenylethyl-N4-[1-(5-chloro-6-methoxy-2-naphthoyl)ethyl]piperazine dihydrochloride

HRID 2055236Notes

Reaction equation

HRID 2055236 reaction equation
[ClH:1].Cl.[C:3]1([CH:9]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)C)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH:18]([CH3:34])[C:19]([C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([O:32][CH3:33])[C:27]=2[Cl:31])[CH:22]=1)=[O:20].[C:35]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[ClH:31].[ClH:1].[C:8]1([CH2:3][CH2:9][N:11]2[CH2:12][CH2:13][N:14]([CH:18]([C:19]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[C:26]([O:32][CH3:33])[C:27]=4[Cl:31])[CH:22]=3)=[O:20])[CH3:34])[CH2:15][CH2:16]2)[CH:35]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 136994292-Bromo-1-(5-chloro-6-methoxynaphthalen-2-yl)propan-1-oneHCID 215377911-(1-Phenylethyl)piperazine dihydrochloride

Product 1

HCID 69200998N1-phenylethyl-N4-[1-(5-chloro-6-methoxy-2-naphthoyl)ethyl]piperazine dihydrochlorideYield 83.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of N-(1-phenylethyl)piperazine dihydrochloride (0.79 g, 3 mmol), 2-bromo-1-(5-chloro-6-methoxynaphthalen-2-yl)propan-1-one (1.64 g, 5 mmol) and K2CO3 (1.38 g, 10 mmol) in acetone was treated according to general preparation 2 to give 1.06 g of compound (IV-43) as white solid, yield 65%, mp 231-232° C. M+ 437.

Workup

  1. additionwas treated
  2. customaccording to general preparation 2

Sources & evidence

ORD record
ord-b659ff3691324a908216390347bb4589
Source dataset
uspto-grants-2008_02
Patent number
US07332495B2

Reaction notes

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