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Toluene → N-ethyl-2-(2,6-dimethoxybenzamidomethyl)pyrrolidine hydrochloride

HRID 224420
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 224420
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[C:8]=1[C:9]([OH:11])=O.C1(C)C=CC=CC=1.[NH2:25][CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][N:28]1[CH2:32][CH3:33]>CC(CC)=O>[ClH:3].[CH2:32]([N:28]1[CH2:29][CH2:30][CH2:31][CH:27]1[CH2:26][NH:25][C:9](=[O:11])[C:8]1[C:12]([O:16][CH3:17])=[CH:13][CH:14]=[CH:15][C:7]=1[O:6][CH3:5])[CH3:33]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 151092,6-Dimethoxybenzoic AcidHCID 24386Thionyl ChlorideHCID 1172952-Aminomethyl-1-ethylpyrrolidine

Produkt 1

HCID 15565705N-ethyl-2-(2,6-dimethoxybenzamidomethyl)pyrrolidine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569
Methyl Ethyl Ketone
Lösungsmittel

Versuchsvorschrift

30 ml of thionyl chloride is added to 18.2 g (0.1 mol) of 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 12.8 g (0.1 mol) of 2-(aminomethyl)-1-ethyl-pyrrolidine in 50 ml methylethyl ketone. After the addition the mixture is stirred for 30 minutes at room temperature. The obtained precipitate is filtered off, washed with ether and recrystallized from ethanol - isopropyl ether. Yield: 26.7 g, m.p. 182°-84° C.

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. additionAfter the addition the mixture
  6. filtrationThe obtained precipitate is filtered off
  7. washwashed with ether
  8. customrecrystallized from ethanol - isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-7acfa7c2db2a4f08802a8102cb5cfeb8
Quelldatensatz
uspto-grants-1980_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04232037

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