Piperazine → 1-(1-Naphthyl)piperazine

HRID 276816Notes

Reaction equation

HRID 276816 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) of piperazine, 38.0 g (339 mM) of potassium tert-butoxide and 50.0 g (241 mM) of 1-bromonaphthalene were added to a mixture of 5.4 g (24.2 mM) of palladium acetate and 14.7 g (48.3 mM) of tri-o-tolylphosphine in 500 ml of xylene, and the mixture was refluxed with efficient stirring 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, mobile phase 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, mobile phase THF/methanol/ammonia 85/13/2)

Sources & evidence

ORD record
ord-6c07b8f12b6141f09e602a421f0d52f1
Source dataset
uspto-grants-2002_03
Patent number
US06355647B1

Reaction notes

Loading…