Methyl 4-bromobenzoate → Methyl 4-(4-acetylpiperazin-1-yl)benzoate

HRID 1911356

Reaktionsgleichung

Reaktionsgleichung von HRID 1911356
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].Br[C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>C1(C)C=CC=CC=1>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 12081Methyl 4-bromobenzoateHCID 62657Potassium Phosphate, TribasicHCID 837951-AcetylpiperazineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl

Produkt 1

HCID 57440409Methyl 4-(4-acetylpiperazin-1-yl)benzoateAusbeute 56,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A deoxygenated suspension of 1-acetylpiperazine (0.308 g, 2.40 mmol), methyl 4-bromobenzoate (0.430 g, 2 mmol), tri-potassium orthophosphate (0.594 g, 2.80 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.164 g, 0.40 mmol) and tris(dibenzylideneacetone)dipaladium(0) (0.092 g, 0.10 mmol) in toluene (10 mL) was stirred at 100° C., over a period of 24 h under nitrogen. The cooled reaction mixture was filtered and evaporated to give crude product. The crude product was purified by silica column chromatography, eluting with a gradient 0-5% MeOH in DCM. Pure fractions were evaporated to dryness to afford methyl 4-(4-acetylpiperazin-1-yl)benzoate (0.295 g, 56.2%) as a yellow solid.

Aufarbeitung

  1. customThe cooled reaction mixture
  2. filtrationwas filtered
  3. customevaporated
  4. customto give crude product
  5. customThe crude product was purified by silica column chromatography
  6. washeluting with a gradient 0-5% MeOH in DCM
  7. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-91f5f87cbe4d43c4b838f5aa7ebe5e19
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08604022B2

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