Toluene → N-Ethyl-2-(3-chloro-2,6-dimethoxybenzamidomethyl)pyrrolidine hydrochloride

HRID 224422

Reaktionsgleichung

Reaktionsgleichung von HRID 224422
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:7]([O:17][CH3:18])=[C:8]([C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)[C:9]([OH:11])=O.C1(C)C=CC=CC=1.[NH2:26][CH2:27][CH:28]1[CH2:32][CH2:31][CH2:30][N:29]1[CH2:33][CH3:34]>C(C(C)=O)C.CCOCC>[ClH:3].[CH2:33]([N:29]1[CH2:30][CH2:31][CH2:32][CH:28]1[CH2:27][NH:26][C:9](=[O:11])[C:8]1[C:12]([O:15][CH3:16])=[CH:13][CH:14]=[C:6]([Cl:5])[C:7]=1[O:17][CH3:18])[CH3:34]

Komponenten

7

Edukt 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 1172952-Aminomethyl-1-ethylpyrrolidineHCID 6121993-Chloro-2,6-dimethoxybenzoic acid

Produkt 1

HCID 15565714N-Ethyl-2-(3-chloro-2,6-dimethoxybenzamidomethyl)pyrrolidine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

30 ml of thionyl chloride is added to 17.0 g (0.078 mol) of 3-chloro-2,6-dimethoxybenzoic acid. The mixture is heated on a steam bath for 30 minutes. To the solution is added 50 ml of toluene. The solvent and excess thionyl chloride is evaporated at reduced pressure. The residue is dissolved in 50 ml of dry methyl ethyl ketone. The solution is added dropwise while stirring to 10.0 g (0.078 mol) of 2-(aminomethyl)-1-ethylpyrrolidine in 50 ml of methyl ethyl ketone. After stirring for 30 minutes at room temperature 150 ml of ether is added. The obtained precipitate is filtered off, washed with ether and recrystallized twice from ethanol - isopropyl ether. Yield: 21.3 g, m.p. 175°-77° C. (first recrystallization). m.p. 179°-80° C. (second recrystallization).

Aufarbeitung

  1. temperatureThe mixture is heated on a steam bath for 30 minutes
  2. customThe solvent and excess thionyl chloride is evaporated at reduced pressure
  3. dissolutionThe residue is dissolved in 50 ml of dry methyl ethyl ketone
  4. additionThe solution is added dropwise
  5. additionis added
  6. filtrationThe obtained precipitate is filtered off
  7. washwashed with ether
  8. customrecrystallized twice from ethanol - isopropyl ether
  9. customYield: 21.3 g, m.p. 175°-77° C. (first recrystallization)
  10. customm.p. 179°-80° C. (second recrystallization)

Quellen und Nachweise

ORD-Eintrag
ord-98866ba79ec8418792784de6733b05ff
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04232037

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