Hydrochloric Acid → HCID 178511717, compound

HRID 271328Notes

Reaction equation

HRID 271328 reaction equation
[C:1]1([CH2:7][CH2:8][O:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([N:16]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN.Cl>C1COCC1.C(O)C>[C:1]1([CH2:7][CH2:8][O:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([NH2:16])[CH2:12][CH2:11]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 178515019HCID 178515019, compound

Product 1

HCID 178511717HCID 178511717, compoundYield 106.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 9 g of trans-2-(4-phenylethyloxy-cyclohexyl)-isoindole-1,3-dione in 60 mL of THF and 150 mL of ethanol was added 3.75 mL of hydrazine hydrate and the mixture heated to reflux for 4 h, then 80 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 2×50 mL of dilute HCl and the combined filtrates basified to pH 10 with 20% sodium hydroxide and extracted with 3×150 mL portions of chloroform. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. Further drying under vacuum gave 6 g of product as an oil. MS (m+1)=220.2; 1H NMR (400 MHz, CDCl3) 7.3-7.1 (m, 5H), 3.7 (t 2H), 3.2 (m, 1H), 2.9 (t, 2H), 2.7 (m, 1H), 2.0 (d, 2H), 1.85 (d, 2H), 1.4 (br s, 2H), 1.3 (dd, 2H), 1.15 (dd, 2H).

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 2×50 mL of dilute HCl
  7. extractionextracted with 3×150 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-b85b5af6ba7d463998f41c5152dfa9c5
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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