Piperazine → 1-(1-Naphthyl)piperazine

HRID 325076Notes

Reaction equation

HRID 325076 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)piperazineYield 42%

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-tolyl-phosphine in 500 ml of xylene, and the mixture was refluxed with efficient stirring under a nitrogen atomsphere for 10 h. The mixture was then diluted with methylene chloride, the insoluble residue was filtered off, and the filtrate was concentrated. The crude product was purified by column chromatography (silica gel, mobile phase THF/methanol/ammonia 85/13/2). 21.5 g (42%) of product with melting point 84-86° C. were isolated.

Workup

  1. temperaturethe mixture was refluxed
  2. filtrationthe insoluble residue was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe crude product was purified by column chromatography (silica gel, mobile phase THF/methanol/ammonia 85/13/2)

Sources & evidence

ORD record
ord-8c2f4a5b79ac43cd8f1135414d7ac940
Source dataset
uspto-grants-2001_04
Patent number
US06222034B1

Reaction notes

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