Hydrazine hydrate (1:1) → [4-(6-aminomethyl-1H-inden-2-yl)-butyl]-dipropyl-amine

HRID 2080740Notes

Reaction equation

HRID 2080740 reaction equation
[CH2:1]([N:4]([CH2:28][CH2:29][CH3:30])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:18][N:19]3C=C4C(C=CC=C4)=C3)[CH:15]=2)[CH:10]=1)[CH2:2][CH3:3].O.NN>CO>[NH2:19][CH2:18][C:14]1[CH:15]=[C:16]2[C:11]([CH:10]=[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:28][CH2:29][CH3:30])[CH2:1][CH2:2][CH3:3])[CH2:17]2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 866149102-[2-(4-dipropylamino-butyl)-3H-inden-5-ylmethyl]-isoindol

Product 1

HCID 23155401[4-(6-aminomethyl-1H-inden-2-yl)-butyl]-dipropyl-amineYield 65.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (82.0 mg) obtained in Example 11-12 was dissolved in methanol (4.1 ml) and added with hydrazine monohydrate (0.082 ml) and the whole was refluxed under heating for 3 hours. The reaction solution was concentrated under reduced pressure. Then, the residue was added with water and subjected to extraction with chloroform. The organic layer was washed with a saturated saline solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (40.1 mg) as a yellow oily substance.

Workup

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 3 hours
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionThen, the residue was added with water
  5. extractionsubjected to extraction with chloroform
  6. washThe organic layer was washed with a saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-c13f1557c993480daa9715a205cd9c4c
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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