Sodium Hydroxide → HCID 53987266, compound

HRID 397743Notes

Reaction equation

HRID 397743 reaction equation
C([N:3]1[CH2:8][CH2:7][C:6]([CH3:19])([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH:16]([CH3:18])[CH3:17])[CH:10]=2)[CH2:5][CH2:4]1)C.Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22].[OH-].[Na+]>C1(C)C=CC=CC=1>[C:24]1([O:23][C:21]([N:3]2[CH2:8][CH2:7][C:6]([CH3:19])([C:9]3[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH:16]([CH3:17])[CH3:18])[CH:10]=3)[CH2:5][CH2:4]2)=[O:22])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 15891Phenyl chloroformateHCID 22707934HCID 22707934, compound

Product 1

HCID 53987266HCID 53987266, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
45 °C

Procedure

To N-ethyl-4-methyl-4-(3-(1-methylethoxy)phenyl)piperidine (Preparation 51, 3.98 g, 15.23 mmol) in toluene (30 ml) at 85° C. was slowly added phenyl chloroformate (2.1 ml, 16.75 mmol) and the mixture was then heated under reflux for 16 h. The solution was cooled to 45° C. and 50% w:v aqueous sodium hydroxide solution (2 ml) was added. Once the solution had cooled to room temperature the organic layer was separated and washed with methanol:1N aqueous hydrochloric acid (1:1, 3×10 ml), methanol:1N aqueous sodium hydroxide solution (1:1, 12 ml) and water (20 ml). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give the crude product. This was purified by silica column chromatography using ethyl acetate:hexane (20:80) to give the title compound as an oil (2.5 g, 45% over three steps).

Workup

  1. customat 85° C.
  2. temperaturethe mixture was then heated
  3. temperatureunder reflux for 16 h
  4. temperatureOnce the solution had cooled to room temperature the organic layer
  5. customwas separated
  6. washwashed with methanol
  7. dry with materialThe organic layer was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give the crude product
  11. customThis was purified by silica column chromatography

Sources & evidence

ORD record
ord-9200e66a11eb40cdb76985c5166693b9
Source dataset
uspto-grants-2003_08
Patent number
US06610711B2

Reaction notes

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