Piperazine → 1-(1-Naphthyl)piperazine

HRID 1935467Notes

Reaction equation

HRID 1935467 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.CC(C)([O-])C.[K+].Br[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1>C1(C)C(C)=CC=CC=1.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:22]1([N:1]2[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)[C:23]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 3

HCID 4837PiperazineHCID 70011-BromonaphthaleneHCID 23665647Potassium tert-butoxide

Product 1

HCID 13421-(1-Naphthyl)piperazine

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6344DichloromethaneSolventHCID 7237O-XyleneSolvent

Procedure

83.2 g (966 mmol) of piperazine, 38.0 g (339 mmol) of potassium tert-butoxide and 50.0 g (241 mmol) of 1-bromonaphthalene were added to a mixture of 5,4 g (24.2 mmol) of palladium acetate and 14.7 g (48.3 mmol) of tri-o-tolylphosphipe in 500 ml of xylene, and the reaction mixture was heated at reflux for 10 h, while stirring thoroughly and under a nitrogen atmosphere. After that, the mixture was diluted with methylene chloride, the insoluble residues were filtered off and the filtrate was evaporated. The crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia 85/13/2). 21.5 g (42%) of product having a m.p. of 84-86° C. were isolated.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 10 h
  3. filtrationthe insoluble residues were filtered off
  4. customthe filtrate was evaporated
  5. customThe crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia 85/13/2)
  6. customwere isolated

Sources & evidence

ORD record
ord-259e17d2c5b1445d8a7cf4ad0ed17099
Source dataset
uspto-grants-2002_05
Patent number
US06387912B1

Reaction notes

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