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 1174012Notes

Reaction equation

HRID 1174012 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 125-5 was dissolved in a 40% methylamine/methanol solution (1.8 ml) and 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 viscous 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-a265f4f67a294f5087b76dd0108644c5
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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