Nitrogen → 4-(4-Benzyl-piperazin-1-YL)-benzoic acid methyl ester

HRID 478631Notes

Reaction equation

HRID 478631 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC([O-])(C)C.[Na+].O=O.N#N.[CH3:39][O:40][C:41](=[O:49])[C:42]1[CH:47]=[CH:46][C:45](Br)=[CH:44][CH:43]=1.[CH2:50]([N:57]1[CH2:62][CH2:61][NH:60][CH2:59][CH2:58]1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>C1(C)C=CC=CC=1.C(OCC)C.C(OC(=O)C)C>[CH3:39][O:40][C:41](=[O:49])[C:42]1[CH:47]=[CH:46][C:45]([N:60]2[CH2:61][CH2:62][N:57]([CH2:50][C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[CH2:58][CH2:59]2)=[CH:44][CH:43]=1

Participants

10

Reactant 6

HCID 947NitrogenHCID 977OxygenHCID 12081Methyl 4-bromobenzoateHCID 759941-BenzylpiperazineHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxide

Product 1

HCID 534068034-(4-Benzyl-piperazin-1-YL)-benzoic acid methyl ester

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tris-(dibenzylidene-acetone)-dipalladium (0.03 mmol), (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (0.9 mmol) and NaOtBu (6.5 mmol) are suspended in toluene (20 ml) in an oxygen-free atmosphere (N2). 4-Bromo-benzoic acid methyl ester (4.65 mmol) and 1-(benzyl)-piperazine (5.6 mmol) are added and the stirred mixture is heated under reflux for 4 hours. After cooling, a mixture of ethylacetate and diethylether is added and the mixture is filtered. Then the solvent is evaporated and the residue is suspended in diethylether and the solid filtered of and dried (vacuum). A pale powder with mp. 105-107° C., Rf=0.67 (CH2Cl2/MeOH=95:5) is obtained.

Workup

  1. temperaturethe stirred mixture is heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling
  4. additionis added
  5. filtrationthe mixture is filtered
  6. customThen the solvent is evaporated
  7. filtrationthe solid filtered of and
  8. customdried (vacuum)
  9. customA pale powder with mp. 105-107° C., Rf=0.67 (CH2Cl2/MeOH=95:5) is obtained

Sources & evidence

ORD record
ord-8666121ee238419cbc06720dd0372e67
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Reaction notes

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