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

HRID 982844Notes

Reaction equation

HRID 982844 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 1 N NaOH solution (20 ml) and extracted with ethyl acetate. The organic phase was 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 1 N NaOH solution (20 ml)
  6. extractionextracted with ethyl acetate
  7. washThe organic phase was washed with brine
  8. dry with materialdried over magnesium sulphate
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-f9976f634f904d53b29c924c80e6e568
Source dataset
uspto-grants-2005_03
Patent number
US06861440B2

Reaction notes

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