Piperazine → 1-(1-Naphthyl)piperazine

HRID 1274994Notes

Reaction equation

HRID 1274994 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 (2.41 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-ae1a949520ef41f6b4f93562b606cc0b
Source dataset
uspto-grants-2000_12
Patent number
US06159981

Reaction notes

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