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

HRID 2080738Notes

Reaction equation

HRID 2080738 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 130.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (189 mg) obtained in Example 11-10 was dissolved in DMF (5.6 ml) and added with potassium carbonate (108.5 mg) and carbethoxyphthalimide (172.0 mg) and the whole was stirred at room temperature for 3 hours. The reaction solution was added with water and subjected to extraction with chloroform. The extract was 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 mg) as a yellow oily substance.

Workup

  1. extractionsubjected to extraction with chloroform
  2. dry with materialThe extract was dried 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-0c54291cbe6a4b79a2fbcb59cf7bfafd
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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