Acetone → N1-benzyl-N4-(5-chloro-6-methoxy-2-naphthoylmethyl)piperazine dihydrochloride

HRID 2102493Notes

Reaction equation

HRID 2102493 reaction equation
[ClH:1].Cl.[CH2:3]([N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.BrCC([C:20]1[C:29]2[C:24](=[C:25]([Cl:32])[C:26]([O:30][CH3:31])=[CH:27][CH:28]=2)[CH:23]=[CH:22][CH:21]=1)=O.C([O-])([O-])=O.[K+].[K+].[CH3:39][C:40](C)=[O:41]>>[ClH:32].[ClH:1].[CH2:3]([N:10]1[CH2:15][CH2:14][N:13]([CH2:39][C:40]([C:21]2[CH:22]=[CH:23][C:24]3[C:29](=[CH:28][CH:27]=[C:26]([O:30][CH3:31])[C:25]=3[Cl:32])[CH:20]=2)=[O:41])[CH2:12][CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 12198046Piperazine, 1-(phenylmethyl)-, hydrochloride (1:2)HCID 867609342-Bromo-1-(5-chloro-6-methoxynaphthalen-1-yl) ethanone

Product 1

HCID 69057176N1-benzyl-N4-(5-chloro-6-methoxy-2-naphthoylmethyl)piperazine dihydrochloride

Procedure

A mixture of N-benzylpiperazine dihydrochloride (2 g, 9.4 mmol), 2-bromo-1-(5-chloro-6-methoxynaphthalen-1-yl) ethanone (3.54 g, 11.3 mmol) and K2CO3 (4.55 g, 33 mmol) in acetone (120 ml) was treated according to the general preparation 2 to obtain N1-benzyl-N4-(5-chloro-6-methoxy-2-naphthoylmethyl) piperazine dihydro-chloride (2.85 g). The above product (2.6 g, 30 mmol) was reduced with NaBH4 (2.22 g, 60 mmol) in methanol (150 ml) according to the general preparation 3 to obtain 10.2 g of the title compound as white solid.

Workup

  1. additionwas treated
  2. customaccording to the general preparation 2

Sources & evidence

ORD record
ord-60885247b96149d39d256c34dee60e82
Source dataset
uspto-grants-2009_08
Patent number
US07576086B2

Reaction notes

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