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

HRID 1029824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1029824
[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 67,3 %

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 (9.7 g), 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. ##STR319##

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

Quellen und Nachweise

ORD-Eintrag
ord-709c1da433d34ccb9216e5fe36296b87
Quelldatensatz
uspto-grants-1992_04
Patentnummer
US05103022

Notizen zur Reaktion

Wird geladen…