Water → 2-[2-(4-Dipropylaminobutyl)-1-methoxymethoxy-indan-5-ylmethyl]-isoindole-1,3-dione

HRID 348765Notes

Reaction equation

HRID 348765 reaction equation
N[CH2:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[CH:8]([O:12][CH2:13][O:14][CH3:15])[CH:7]([CH2:16][CH2:17][CH:18](N(CCC)CCC)[CH3:19])[CH2:6]2.C(=O)([O-])[O-].[K+].[K+].C([C:38]1[CH:48]=[CH:47][CH:46]=[C:40]2[C:41]([NH:43][C:44](=[O:45])[C:39]=12)=[O:42])(OCC)=O.O>CN(C=O)C>[CH2:41]([N:43]([CH2:44][CH2:39][CH3:38])[CH2:19][CH2:18][CH2:17][CH2:16][CH:7]1[CH2:6][C:5]2[C:9](=[CH:10][CH:11]=[C:3]([CH2:2][N:43]3[C:44](=[O:45])[C:39]4[C:40](=[CH:46][CH:47]=[CH:48][CH:38]=4)[C:41]3=[O:42])[CH:4]=2)[CH:8]1[O:12][CH2:13][O:14][CH3:15])[CH2:40][CH3:46]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 22254400EthoxycarbonylphthalimideHCID 230793035-Aminomethyl-2-(3-dipropylaminobutyl)-1-methoxymethoxy-indane

Product 1

HCID 231555482-[2-(4-Dipropylaminobutyl)-1-methoxymethoxy-indan-5-ylmethyl]-isoindole-1,3-dioneYield 131.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (189.7 mg) obtained in Example 127-10 was dissolved in DMF (5.69 ml) and added with potassium carbonate (108.5 mg) and carbethoxyphthalimide (172.0 mg), followed by stirring at room temperature for 3 hours. The reaction solution was added with water. Then, the solution was 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/methanol), thereby obtaining the subject compound (253.9 mg) as a yellow oily substance.

Workup

  1. extractionThen, the solution was subjected to separation/extraction with chloroform
  2. dry with materialdried with anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-a064a0dc0a09444d8b0b9183261770fd
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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