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

HRID 1029824Notes

Reaction equation

HRID 1029824 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 199012002-Methyl-1-(2,3-dimethylphenyl)-3-pyrrolidino-1-propanone hydrochlorideYield 67.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

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##

Workup

  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

Sources & evidence

ORD record
ord-709c1da433d34ccb9216e5fe36296b87
Source dataset
uspto-grants-1992_04
Patent number
US05103022

Reaction notes

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