Hydrochloric Acid → HCID 178511719, compound

HRID 271334Notes

Reaction equation

HRID 271334 reaction equation
[F:1][CH:2]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:7][CH2:6]1.O.NN.Cl>C1COCC1.C(O)C>[F:1][CH:2]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:3][O:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([NH2:11])[CH2:9][CH2:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 178515020HCID 178515020, compound

Product 1

HCID 178511719HCID 178511719, compoundYield 88.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.7 g of racemic trans-2-[4-(2-fluoro-2-phenyl-ethoxy)-cyclohexyl]-isoindole-1,3-dione in 15 mL of THF and 15 mL of ethanol was added 0.3 mL of hydrazine hydrate and the mixture heated to reflux for 4 h, then 5 mL of 6N HCl was added and the reflux was continued for 1 h. The cooled mixture was concentrated under reduced pressure to remove ethanol and filtered. The filter pad was washed with 2×10 mL of dilute HCl and the combined filtrates basified to pH 10 with 20% sodium hydroxide and extracted with 3×25 mL portions of chloroform. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. Further drying under vacuum gave 0.4 g of product as an oil. MS (m+1)=238.3.

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 4 h
  3. concentrationThe cooled mixture was concentrated under reduced pressure
  4. customto remove ethanol
  5. filtrationfiltered
  6. washThe filter pad was washed with 2×10 mL of dilute HCl
  7. extractionextracted with 3×25 mL portions of chloroform
  8. dry with materialThe combined extracts were dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customFurther drying under vacuum

Sources & evidence

ORD record
ord-926955d63326440c8ded577a485961a6
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

Loading…