Hydrochloric Acid → HCID 19763365, compound

HRID 248343Notes

Reaction equation

HRID 248343 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][N:16]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.NN.Cl.O>CCO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][NH2:16])[CH2:11][CH2:12]2)=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 9321HydrazineHCID 19763375HCID 19763375, compound

Product 1

HCID 19763365HCID 19763365, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

13.8 g (0.04 mol) of 2-{3-[4-(4-fluorophenoxy)-1-piperidyl]propyl}-1H-isoindole-1,3(2H)-dione and 3.9 ml (0.08 mol) of hydrazine in 280 ml of EtOH are reacted for 3 h at the refluxing temperature, and the mixture is then left overnight. 15 ml of concentrated HCl and 20 ml of H2O are then introduced. The mixture is left for 3 hours at the refluxing temperature, then filtered and concentrated. The residue is taken up with water, filtered and rinsed with water. The filtrate is washed twice with ether, then alkalinised with NaOH and extracted 3 times with CH2Cl2. The solution is dried over Na2SO4, filtered and concentrated.

Workup

  1. waitThe mixture is left for 3 hours at the refluxing temperature
  2. filtrationfiltered
  3. concentrationconcentrated
  4. filtrationfiltered
  5. washrinsed with water
  6. washThe filtrate is washed twice with ether
  7. extractionextracted 3 times with CH2Cl2
  8. dry with materialThe solution is dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-db9ba375069a4b22aa6be5909382bacf
Source dataset
uspto-grants-1993_05
Patent number
US05210086

Reaction notes

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