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

HRID 2249605Notes

Reaction equation

HRID 2249605 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 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 1N 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-ca2e3ae8b26b49fa83baf0c3d632d12b
Source dataset
uspto-grants-2008_01
Patent number
US07314884B2

Reaction notes

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