Piperazine → 1-(1-Naphthyl)piperazine

HRID 1935478Notes

Reaction equation

HRID 1935478 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=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>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

8

Reactant 4

HCID 4837PiperazineHCID 70011-BromonaphthaleneHCID 80271Tri-o-tolylphosphineHCID 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-tolylphosphine in 500 ml of xylene, and the reaction mixture was heated at reflux for 10 h under a nitrogen atmosphere and while stirring thoroughly. 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 under a nitrogen atmosphere
  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-8be1bce1dbbb44ceaf38d70a3f41cc12
Source dataset
uspto-grants-2002_05
Patent number
US06387912B1

Reaction notes

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