2-[2-(4-dipropylaminobutyl)-3-propyl-3H-benzimidazol-5-ylmethyl]isoindole-1,3-dione → [4-(6-aminomethyl-1-propyl-1H-benzimidazol-2-yl)butyl]dipropylamine

HRID 2080718Notes

Reaction equation

HRID 2080718 reaction equation
[CH2:1]([N:4]([CH2:33][CH2:34][CH3:35])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]1[N:10]([CH2:30][CH2:31][CH3:32])[C:11]2[CH:17]=[C:16]([CH2:18][N:19]3C(=O)C4C(=CC=CC=4)C3=O)[CH:15]=[CH:14][C:12]=2[N:13]=1)[CH2:2][CH3:3]>CN.CO>[NH2:19][CH2:18][C:16]1[CH:15]=[CH:14][C:12]2[N:13]=[C:9]([CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:33][CH2:34][CH3:35])[N:10]([CH2:30][CH2:31][CH3:32])[C:11]=2[CH:17]=1

Participants

3

Reactant 1

HCID 231555012-[2-(4-dipropylaminobutyl)-3-propyl-3H-benzimidazol-5-ylmethyl]isoindole-1,3-dione

Product 1

HCID 23079304[4-(6-aminomethyl-1-propyl-1H-benzimidazol-2-yl)butyl]dipropylamineYield 103.5%

Reagents, catalysts & solvents 1

HCID 57454252Monomethylamine methanolSolvent

Procedure

The compound (173 mg) obtained in Example 3-5 was dissolved in a 40% methylamine/methanol solution (1.8 ml) and the whole was stirred at room temperature for 17 hours. After completion of the reaction, the solvent was distilled off under reduced pressure and the residue was then purified through silica gel column chromatography (chloroform/ethyl acetate), thereby obtaining the subject compound (130 mg) as a pale-yellow oily substance.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe residue was then purified through silica gel column chromatography (chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-477cd88fd69949bea9765939113ec834
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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