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

HRID 478628

반응식

HRID 478628 반응식
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

참가 물질

8

반응물 6

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

생성물 1

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

시약·촉매·용매 1

HCID 80711,2-Dimethoxyethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9c327ad5f7cf4604b824c2e783901015
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642239B2

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