Hydrazine hydrate (1:1) → HCID 178510930, compound

HRID 1716552Notes

Reaction equation

HRID 1716552 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][N:15]3C(=O)C4C(=CC=CC=4)C3=O)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.NN>C(O)C>[C:1]1([C:7]2[NH:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][NH2:15])[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178514988HCID 178514988, compound

Product 1

HCID 178510930HCID 178510930, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of 2-[3-(2-phenyl-1H-imidazol-4-yl)-propyl]-isoindole-1,3-dione (4.16 g) in ethanol (50 ml) was added hydrazine hydrate (3.18 g). The reaction mixture was stirred under reflux for 4 h, cooled down to 0-5° C., and the precipitate was filtered off. The filtrate was concentrated, and the oily residue was quenched with cooled 1N NaOH solution (20 ml) and extracted with ethyl acetate. The organic phase washed with brine, dried over magnesium sulphate and concentrated to dryness to obtain 3-(2-phenyl-1H-imidazol-4-yl)-propylamine (1.95 g) as a yellow foam, which was sufficiently pure to be used directly in the next step.

Workup

  1. temperatureunder reflux for 4 h
  2. filtrationthe precipitate was filtered off
  3. concentrationThe filtrate was concentrated
  4. customthe oily residue was quenched
  5. temperaturewith cooled 1N NaOH solution (20 ml)
  6. extractionextracted with ethyl acetate
  7. washThe organic phase washed with brine
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3a42844c146c43f3b5fed50a785344f8
Source dataset
uspto-grants-2010_09
Patent number
US07803819B2

Reaction notes

Loading…