Acetic Acid → HCID 18694312, compound

HRID 1870867Notes

Reaction equation

HRID 1870867 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH2:4][C:5]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(O)[CH2:6]2.C(O)(=O)C.Cl.[C:22]([OH:28])(=[O:27])[CH2:23][C:24]([OH:26])=[O:25]>C(O)C>[C:22]([OH:28])(=[O:27])[CH2:23][C:24]([OH:26])=[O:25].[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH:3]1[CH:4]=[C:5]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH2:6]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 867Malonic AcidHCID 339047HCID 339047, compound

Product 1

HCID 18694312HCID 18694312, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared from 8-methyl-3-phenyl-8-azabicyclo[3.2.1]octan-3-ol (8 g, 37 mmol), glacial acetic acid (25 mL) and concentrated hydrochloric acid (8 mL). The free base of the title compound (7.4 g, 37 mmol) was dissolved in absolute ethanol (20 mL) and added malonic acid (3.9 g, 37.5 mmol), the solution was heated at reflux for a couple of minutes, some impurities was removed by filtration while the solution was still hot, the solution was cooled and kept at 5° C. for at while, then seeded with a crystal and precipitation of the title compound began, after 2 hours at 5° C., the title compound was isolated by filtration, the crystals was washed with cold absolute ethanol (10 mL). Yield 5.9 g (53%), m.p. 131-131.8° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for a couple of minutes
  3. customsome impurities was removed by filtration while the solution
  4. temperaturethe solution was cooled
  5. customkept at 5° C. for at while
  6. customseeded with a crystal and precipitation of the title compound
  7. customthe title compound was isolated by filtration

Sources & evidence

ORD record
ord-6cdc7af2ccba46fdaac1f07c6636cfaf
Source dataset
uspto-grants-2000_08
Patent number
US06100275

Reaction notes

Loading…