2,5-Dichloronitrobenzene → Escitalopram Oxalate

HRID 1669960

Reaktionsgleichung

Reaktionsgleichung von HRID 1669960
[CH3:1][N:2]([CH3:25])[CH2:3][CH2:4][CH2:5][C:6]([C:15]1[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][C:16]=1[CH2:23]O)([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1)[OH:7].C([O-])([O-])=O.[K+].[K+].ClC1C=CC(Cl)=CC=1[N+]([O-])=O.O.O.[C:45]([OH:50])(=[O:49])[C:46]([OH:48])=[O:47]>CS(C)=O.CC(C)=O.O>[CH3:25][N:2]([CH2:3][CH2:4][CH2:5][C@@:6]1([C:8]2[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=2)[O:7][CH2:23][C:16]2[CH:17]=[C:18]([C:19]#[N:20])[CH:21]=[CH:22][C:15]1=2)[CH3:1].[C:46]([OH:48])([C:45]([OH:50])=[O:49])=[O:47]

Komponenten

8

Edukt 4

HCID 69772,5-DichloronitrobenzeneHCID 11430Potassium CarbonateHCID 61373Oxalic acid dihydrateHCID 101321644-(4-(Dimethylamino)-1-(4-fluorophenyl)-1-hydroxybutyl)-3-(hydroxymethyl)benzonitrile

Produkt 1

HCID 146571Escitalopram Oxalate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 10 gm of (RS)-(±)4-[4-(dimethylamino)-1-(4-fluorophenyl)-1-hydroxy-1-butyl]-3-(hydroxymethyl)-benzonitrile in 50 ml of dimethylsulfoxide (DMSO) at room temperature was added 12 gm of anhydrous K2CO3 and 6.73 gm of 2,5-dichloronitrobenzene was added to the above reaction mixture at room temperature and stirred at 100° C. for 15 hours. To the reaction mixture, 250 ml of water was added and extracted with toluene, the toluene layer was washed with water and 5% sodium hydroxide solution and after acid base treatment yielded an oily product. The oil was dissolved in 40 ml of acetone at 30° C. and 3.4 gm of oxalic acid dihydrate was added to it, stirred, cooled, filtered and dried at 60° C.

Aufarbeitung

  1. additionwas added to the above reaction mixture at room temperature
  2. extractionextracted with toluene
  3. washthe toluene layer was washed with water and 5% sodium hydroxide solution
  4. customafter acid base treatment yielded an oily product
  5. stirringstirred
  6. temperaturecooled
  7. filtrationfiltered
  8. customdried at 60° C.

Quellen und Nachweise

ORD-Eintrag
ord-bf7ce9483cc84f19808ba628cf211867
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07989645B2

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