Phosphoric Acid → HCID 9837986, compound

HRID 1871907Notes

Reaction equation

HRID 1871907 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH3:11][N:12]1[CH:16]2[CH2:17][C:18]([CH2:20][CH:13]1[CH2:14][CH2:15]2)=O.P(=O)(O)(O)O.[OH-].[Na+]>C(O)(=O)C>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:18]3[CH2:17][CH:16]4[N:12]([CH3:11])[CH:13]([CH2:14][CH2:15]4)[CH:20]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1004Phosphoric AcidHCID 14798Sodium HydroxideHCID 79038Npc164516HCID 3512786-Fluoroindole

Product 1

HCID 9837986HCID 9837986, compoundYield 9.44%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
62.5 °C

Procedure

A solution of 2.0 gm (14.8 mMol) 6-fluoroindole in 50 mL acetic acid was heated to 55° C. and vigorously deoxygen-ated with nitrogen. To this reaction mixture were then added 4.12 gm (29.6 mMol) tropinone and 12.3 mL 2N phosphor-ic acid. The resulting mixture was heated at 60-65° C. for 24 hours. The reaction mixture was cooled to room temperature and then poured into ice containing about 300 mL acetic acid. The pH of this mixture was then adjusted to about 8 by the addition of 50% aqueous NaOH. The resulting mixture was extracted well with dichloromethane. The combined organic extracts were washed with saturated aqueous sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with a gradient of dichlorometh-ane containing 30% dichloromethane saturated with ammonia and from 1-15% methanol. Fractions containing product were combined and concentrated under reduced pressure. The solid residue was crystallized from ethanol to provide 0.358 gm (9.44%) of the title compound as colorless crystals.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe resulting mixture was extracted well with dichloromethane
  3. washThe combined organic extracts were washed with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluting with a gradient of dichlorometh-ane containing 30% dichloromethane saturated with ammonia and from 1-15% methanol
  7. additionFractions containing product
  8. concentrationconcentrated under reduced pressure
  9. customThe solid residue was crystallized from ethanol

Sources & evidence

ORD record
ord-6881591772f94ac59e51b4361cd3e441
Source dataset
uspto-grants-2000_08
Patent number
US06107307

Reaction notes

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