Methanol → HCID 19823619, compound

HRID 1650937Notes

Reaction equation

HRID 1650937 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH:12]([N:18]([CH3:20])[CH3:19])[C:13](=[O:17])[CH:14]([CH3:16])[CH3:15])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(O)(=O)C(O)=O.CO>O>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([CH:12]([N:18]([CH3:20])[CH3:19])[C:13](=[O:17])[CH:14]([CH3:15])[CH3:16])[CH2:9][CH2:10][CH2:11]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 971Oxalic AcidHCID 19823620HCID 19823620, compound

Product 1

HCID 19823619HCID 19823619, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylamino-3-methylbutan-2-one (1 g prepared in a similar manner to that described in Example 47 and having a boiling point range 144°-148° C./2 mm Hg) was heated under reflux for 20 minutes with a mixture of 30% aqueous oxalic acid solution (9 ml) and methanol (90 ml). The reaction mixture was poured into water and the aqueous mixture was washed with ether, basified and extracted with ether. The solvent was removed from the dried ethereal extract and the residue was treated with a mixture of excess concentrated hydrochloric acid and propan-2-ol. Removal of the solvents gave a residue which was dried by azeotropic distillation with propan-2-ol. The residue was then triturated with acetone to give a solid which was recrystallised twice from propan-2-ol to give 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylamino-3-methylbutan-2-one hydrochloride (m.p. 202°-204° C.).

Workup

  1. customrange 144°-148° C.
  2. temperaturewas heated
  3. washthe aqueous mixture was washed with ether
  4. extractionextracted with ether
  5. customThe solvent was removed from the dried ethereal
  6. extractionextract
  7. additionthe residue was treated with a mixture of excess concentrated hydrochloric acid and propan-2-ol
  8. customRemoval of the solvents
  9. customgave a residue which
  10. dry with materialwas dried by azeotropic distillation with propan-2-ol
  11. customThe residue was then triturated with acetone
  12. customto give a solid which
  13. customwas recrystallised twice from propan-2-ol

Sources & evidence

ORD record
ord-cf139085f644487ea609f8cc505d35cf
Source dataset
uspto-grants-1990_05
Patent number
US04925879

Reaction notes

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