Piperazine → 1-(1-Naphthyl)piperazine

HRID 1274842Notes

Reaction equation

HRID 1274842 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 mM [sic]) of piperazine, 38.0 g (339 mM [sic]) of potassium tert-butoxide and 50.0 g (241 mM [sic]) of 1-bromonaphthalene were added to a mixture of 5.4 g (24.2 mM [sic]) of palladium acetate and 14.7 g (48.3 mM [sic]) of tri-o-tolylphosphine in 500 ml of xylene, and the mixture was refluxed while stirring vigorously under a nitrogen atmosphere for 10 h. The mixture was then diluted with methylene chloride, the insoluble residues were filtered off, and the filtrate was concentrated. The crude product was purified by column chromatography (silica gel, eluent THF/methanol/ammonia 85/13/2). 21.5 g (42%) of product were isolated with melting point 84-86° C.

Workup

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

Sources & evidence

ORD record
ord-8dab580654ff4178af892408a29410bd
Source dataset
uspto-grants-2000_12
Patent number
US06159962

Reaction notes

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