Dimethyl Sulfoxide → Ethyl 4-(3-dimethylaminopyrrolidin-1-yl)benzoate

HRID 2251293Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2251293
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[CH3:13][N:14]([CH3:20])[CH:15]1[CH2:19][CH2:18][NH:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[CH3:13][N:14]([CH3:20])[CH:15]1[CH2:19][CH2:18][N:17]([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH2:16]1

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 27585193-(Dimethylamino)pyrrolidine

Produkt 1

HCID 69209289Ethyl 4-(3-dimethylaminopyrrolidin-1-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of ethyl 4-fluorobenzoate (4.47 g), dimethylpyrrolidin-3-ylamine (3.04 g), potassium carbonate (3.68 g) and dimethyl sulfoxide (20 ml) was heated at 130° C. for 7 hours. After cooling, the mixture was diluted with water and extracted with methyl tert-butyl ether. The organic phase was washed with water, dried over magnesium sulfate, filtered and concentrated. The product with the molecular weight of 262.35 (C15H22N2O2) was obtained in this way; MS (ESI): 263 (M+H+).

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionextracted with methyl tert-butyl ether
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product with the molecular weight of 262.35 (C15H22N2O2) was obtained in this way

Quellen und Nachweise

ORD-Eintrag
ord-2e0f1b24075b430493da6a6ef4370264
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07319108B2

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