Acetic Acid → 1-[(2-Propyl-benzimidazol-1-yl)methyl]-4-propylpyrrolidin-2-one

HRID 1295820Notes

Reaction equation

HRID 1295820 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][CH2:9][N:10]1[CH2:14][CH:13]([CH2:15][CH2:16][CH3:17])[CH2:12][C:11]1=[O:18].[CH:19](=O)[CH2:20][CH3:21].[C:23](O)(=O)C>O1CCOCC1>[CH2:20]([C:21]1[N:8]([CH2:9][N:10]2[CH2:14][CH:13]([CH2:15][CH2:16][CH3:17])[CH2:12][C:11]2=[O:18])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1)[CH2:19][CH3:23]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 527PropanalHCID 58911264(2-Aminophenyl){(2-oxo-4-propyl-pyrrolidin-1-yl)methyl}amine

Product 1

HCID 111623591-[(2-Propyl-benzimidazol-1-yl)methyl]-4-propylpyrrolidin-2-oneYield 33%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a 50 ml three necked flask fitted with a magnetic stirrer, under inert atmosphere, a solution of (2-aminophenyl){(2-oxo-4-propyl-pyrrolidin-1-yl)methyl}amine a29 (1 eq, 0.69 mmol, 170 mg), propionaldehyde (1.4 eq, 0.966 mmol, 56 mg, 71 μl), acetic acid (0.3 ml) and dioxane (4 ml) was heated at 65° C. during 40 h. After cooling to room temperature, the solvent was removed under vacuum and the crude product was purified by preparative thin layer chromatography (CH2Cl2/MeOH/NH4OH: 96/3.6/0.4) to give of 1-[(2-propyl)-benzimidazol-1-yl)methyl]-4-propylpyrrolidin-2-one 94 (65 mg, 33%).

Workup

  1. customthe solvent was removed under vacuum
  2. customthe crude product was purified by preparative thin layer chromatography (CH2Cl2/MeOH/NH4OH: 96/3.6/0.4)

Sources & evidence

ORD record
ord-0642517aa48f4a0393ec5537388a2c7b
Source dataset
uspto-grants-2007_07
Patent number
US07244747B2

Reaction notes

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