Triethylamine → N1-benzyl-N4-[1-(5-chloro-6-methoxy-2-naphthoyl)ethyl] piperazine dihydrochloride

HRID 2102495Notes

Reaction equation

HRID 2102495 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.Br[CH:17]([CH3:33])[C:18]([C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([O:31][CH3:32])[C:26]=2[Cl:30])[CH:21]=1)=[O:19].C(N(CC)CC)C>C1C=CC=CC=1>[ClH:30].[ClH:1].[CH2:3]([N:10]1[CH2:15][CH2:14][N:13]([CH:17]([C:18]([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[C:25]([O:31][CH3:32])[C:26]=3[Cl:30])[CH:21]=2)=[O:19])[CH3:33])[CH2:12][CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12198046Piperazine, 1-(phenylmethyl)-, hydrochloride (1:2)HCID 136994292-Bromo-1-(5-chloro-6-methoxynaphthalen-2-yl)propan-1-one

Product 1

HCID 69055806N1-benzyl-N4-[1-(5-chloro-6-methoxy-2-naphthoyl)ethyl] piperazine dihydrochlorideYield 101.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of N-benzyl piperazine dihydrochloride (1.5 g, 7.05 mmol), 2-bromo-1-(5-chloro-6-methoxynaphthalen-2-yl) propan-1-one (2.8 g, 8.5 mmol) and triethyl-amine (2.38 g, 23.5 mmol) in benzene (150 ml) was treated according to the general preparation 2 to obtain 2.14 g of N1-benzyl-N4-[1-(5-chloro-6-methoxy-2-naphthoyl)ethyl] piperazine dihydrochloride, yield 60%, mp 252-253° C.).

Workup

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

Sources & evidence

ORD record
ord-bf51c1241d4e4a97a06792b98dc794d7
Source dataset
uspto-grants-2009_08
Patent number
US07576086B2

Reaction notes

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