Hydrazine hydrate (1:1) → HCID 178459267, compound

HRID 1363718Notes

Reaction equation

HRID 1363718 reaction equation
O.NN.[CH2:4]([O:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([N:14]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:10][CH2:9]1)[CH2:5][CH3:6]>CCO>[CH2:4]([O:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH2:14])[CH2:10][CH2:9]1)[CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178459261HCID 178459261, compound

Product 1

HCID 178459267HCID 178459267, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

Hydrazine hydrate (1.76 g, 55 mmol) was added to a solution of trans-2-(4-propyloxycyclohexyl)-isoindole-1,3-dione (7.90 g, 27.5 mmol) in absolute EtOH (100 mL). The reaction was stirred at 50° C. for 3 h before the reaction mixture was filtered. The solvent was removed in vacuo and Et2O (250 mL) was added after stirring for 30 min the solid was filtered off and the filtrate was added 150 mL 1 N HCl, the phases were separated and the aqueous phase was washed with Et2O (150 mL) before 10 N NaOH was added (until pH=11-12). The aqueous phase was extracted with EtOAc (200 mL+2×100 mL) and the organic fractions were collected and dried (MgSO4) to give 3.11 g (72%) of trans-4-propoxy-cyclohexylamine.

Workup

  1. filtrationwas filtered
  2. customThe solvent was removed in vacuo and Et2O (250 mL)
  3. additionwas added
  4. stirringafter stirring for 30 min the solid
  5. filtrationwas filtered off
  6. additionthe filtrate was added 150 mL 1 N HCl
  7. customthe phases were separated
  8. washthe aqueous phase was washed with Et2O (150 mL) before 10 N NaOH
  9. additionwas added (until pH=11-12)
  10. extractionThe aqueous phase was extracted with EtOAc (200 mL+2×100 mL)
  11. customthe organic fractions were collected
  12. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-68c5470aed6b4e87b1d519f4e9a11fc3
Source dataset
uspto-grants-2011_02
Patent number
US07884210B2

Reaction notes

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