Hydrochloric Acid → 2-Methyl-1-(2,3-dimethylphenyl)-3-pyrrolidino-1-propanone hydrochloride

HRID 345500

Reaktionsgleichung

Reaktionsgleichung von HRID 345500
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](=[O:12])[CH2:10][CH3:11].[CH2:13]=O.[ClH:15].[NH:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1.Cl>C(O)(C)C.O>[ClH:15].[CH3:11][CH:10]([CH2:13][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[C:9]([C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[CH3:1])=[O:12]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 212848Pyrrolidine, hydrochloride (1:1)HCID 123994421-(2,3-Dimethylphenyl)propan-1-one

Produkt 1

HCID 199012002-Methyl-1-(2,3-dimethylphenyl)-3-pyrrolidino-1-propanone hydrochlorideAusbeute 64,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of 1-(2,3-dimethylphenyl)-1-propanone (11.2 g), paraformaldehyde (2.70 g), pyrrolidine-hydrochloride (9.7g), and hydrochloric acid (0.5 ml) in isopropyl alcohol (15 ml) was refluxed for 8.5 hours. The reaction mixture was evaporated in vacuo to give the residue. The residue was dissolved in water and then washed with ethyl acetate. The aqueous layer was extracted with dichloromethane and then dried over anhydrous magnesium sulfate. The mixture was filtered and then the filtrate was evaporated in vacuo to give the residue. The residue was recrystallized from CH2Cl2 - AcOEt to give 2-methyl-1-(2,3-dimethylphenyl)-3-pyrrolidino-1-propanone hydrochloride (13.1 g, Y: 64.7%) as colorless prisms, m.p. 149°-151° C. IR ν (the free base)maxneat : 1690 cm-1 ##STR323##

Aufarbeitung

  1. temperaturewas refluxed for 8.5 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. customto give the residue
  4. washwashed with ethyl acetate
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe mixture was filtered
  8. customthe filtrate was evaporated in vacuo
  9. customto give the residue
  10. customThe residue was recrystallized from CH2Cl2 - AcOEt

Quellen und Nachweise

ORD-Eintrag
ord-c280d2d08684449bb6a22c0779f86dd4
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05057535

Verknüpfte Notizen

Wird geladen…