Hydrazine hydrate (1:1) → [4-(5-Aminomethyl-1-methoxyindan-2-yl)-butyl]-dipropylamine

HRID 348767Notes

Reaction equation

HRID 348767 reaction equation
[CH2:1]([N:4]([CH2:32][CH2:33][CH3:34])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:18][N:19]3C(=O)C4C(=CC=CC=4)C3=O)[CH:15]=2)[CH:10]1[O:30][CH3:31])[CH2:2][CH3:3].O.NN>CO>[NH2:19][CH2:18][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH:10]([O:30][CH3:31])[CH:9]([CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:32][CH2:33][CH3:34])[CH2:1][CH2:2][CH3:3])[CH2:17]2

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 669416822-[2-(4-Dipropylamino-butyl)-1-methoxy-indan-5-ylmethyl]-isoindole-1,3-dione

Product 1

HCID 23079237[4-(5-Aminomethyl-1-methoxyindan-2-yl)-butyl]-dipropylamineYield 65.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (95.7 mg) obtained in Example 127-12 was dissolved in methanol (4.79 ml) and added with hydrazine monohydrate (0.0957 ml), followed by thermal reflux for 1 hour. The reaction solution was concentrated under reduced pressure. Then, the residue was added with water and subjected to separation/extraction with chloroform, 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 (45.0 mg) as a yellow oily substance.

Workup

  1. temperatureby thermal reflux for 1 hour
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionThen, the residue was added with water
  4. extractionsubjected to separation/extraction with chloroform
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-78a034be5b424a31b0bbc76b799f45ef
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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