2-Chlorobenzimidazole → 1-[(2-chloro-1H-benzimidazol-1-yl)methyl]-4-propyl-pyrrolidin-2-one

HRID 1924302Notes

Reaction equation

HRID 1924302 reaction equation
O[CH2:2][N:3]1[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]1=[O:11].C(N(CC)C(=O)OCN1CC(CCC)CC1=O)C.[Cl:30][C:31]1[NH:35][C:34]2[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=2[N:32]=1>C(#N)C>[Cl:30][C:31]1[N:35]([CH2:2][N:3]2[CH2:7][CH:6]([CH2:8][CH2:9][CH3:10])[CH2:5][C:4]2=[O:11])[C:34]2[CH:36]=[CH:37][CH:38]=[CH:39][C:33]=2[N:32]=1

Participants

5

Reactant 3

HCID 785722-ChlorobenzimidazoleHCID 113326021-(Hydroxymethyl)-4-propylpyrrolidin-2-oneHCID 11448237(2-Oxo-4-propylpyrrolidin-1-yl)methyl diethylcarbamate

Product 1

HCID 577430561-[(2-chloro-1H-benzimidazol-1-yl)methyl]-4-propyl-pyrrolidin-2-oneYield 49.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(hydroxymethyl)-4-propylpyrrolidin-2-one x2 (0.472 g, 1 eq, 3 mmol), (2-oxo-4-propylpyrrolidin-1-yl)methyl diethylcarbamate x6 (38.5 mg, 5 mol %, 0.15 mmol) and 2-chloro-1H-benzimidazole x163 (1.2 eq, 3.3 mmol, 0.504 g) in acetonitrile (3 ml) is irradiated in a microwave apparatus (CEM discover) during 0.75 h (100 w). After cooling, evaporation of the solvent under reduce pressure and purification by preparative chromatography on reverse phase, 1-[(2-chloro-1H-benzimidazol-1-yl)methyl]-4-propyl-pyrrolidin-2-one 300 is isolated as a clear oil (0.42 g).

Workup

  1. temperatureAfter cooling
  2. customevaporation of the solvent
  3. custompressure and purification by preparative chromatography on reverse phase

Sources & evidence

ORD record
ord-3f316e074c24469e870cae912a52cc73
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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