Nitrogen → Methyl 4-(4-propan-2-yl-piperazin-1-yl)benzoate

HRID 478628

Reaction equation

HRID 478628 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.C(=O)([O-])[O-].[K+].[K+].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.[CH:50]([N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1)([CH3:52])[CH3:51]>COCCOC>[CH3:39][O:40][C:41](=[O:49])[C:42]1[CH:47]=[CH:46][C:45]([N:56]2[CH2:57][CH2:58][N:53]([CH:50]([CH3:52])[CH3:51])[CH2:54][CH2:55]2)=[CH:44][CH:43]=1

Participants

8

Reactant 6

HCID 947NitrogenHCID 977OxygenHCID 11430Potassium CarbonateHCID 12081Methyl 4-bromobenzoateHCID 780131-IsopropylpiperazineHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl

Product 1

HCID 69129778Methyl 4-(4-propan-2-yl-piperazin-1-yl)benzoate

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Tris-(dibenzylidene-acetone)-dipalladium (0.05 mmol), (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (0.1 mmol) and potassium carbonate (4.6 mmol) are suspended in 1,2-dimethoxyethane (10 ml) in an oxygen-free atmosphere (N2). 4-Bromo-benzoic acid methyl ester (3.3 mmol) and 1-isopropyl-piperazine (3.9 mmol) are added and the stirred mixture is heated under reflux for 28 hours. After cooling the solvent is evaporated and water is added to the residue, which is then extracted three times with ethyl acetate. The combined extract is dried over sodium sulfate and evaporated. The residue is purified by flash chromatography on silica gel with (CH2Cl2/MeOH=95:5) as mobile phase. The product containing fractions are combined and evaporated. The residue is suspended in diethylether/pentane and the solid filtered of and dried (vacuum). A pale-brown powder with Rf=0.23 (CH2Cl2/MeOH=95:5) is obtained.

Workup

  1. temperaturethe stirred mixture is heated
  2. temperatureunder reflux for 28 hours
  3. temperatureAfter cooling the solvent
  4. customis evaporated
  5. additionwater is added to the residue, which
  6. extractionis then extracted three times with ethyl acetate
  7. extractionThe combined extract
  8. dry with materialis dried over sodium sulfate
  9. customevaporated
  10. customThe residue is purified by flash chromatography on silica gel with (CH2Cl2/MeOH=95:5) as mobile phase
  11. additionThe product containing fractions
  12. customevaporated
  13. filtrationthe solid filtered of and
  14. customdried (vacuum)
  15. customA pale-brown powder with Rf=0.23 (CH2Cl2/MeOH=95:5) is obtained

Sources & evidence

ORD record
ord-9c327ad5f7cf4604b824c2e783901015
Source dataset
uspto-grants-2003_11
Patent number
US06642239B2

Linked notes

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