Pyrrolidine → 2-(Pyrrolidin-1-yl)-1H-benzo[d]imidazole

HRID 353814Notes

Reaction equation

HRID 353814 reaction equation
Cl[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[NH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1>C(O)C>[N:11]1([C:2]2[NH:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[N:3]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 785722-Chlorobenzimidazole

Product 1

HCID 69918962-(Pyrrolidin-1-yl)-1H-benzo[d]imidazoleYield 39.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
165 °C

Procedure

2-Chloro-1H-benzimidazole (10.0 g, 0.066 mol), pyrrolidine (18.5 g, 0.26 mol), and ethanol (100 mL) were combined. The resulting solution was heated at 160-170° C. for 6 hours and then the solvent was evaporated. The resulting residue was mixed with water. The mixture was made strongly acidic with hydrochloric acid and then made basic with ammonium hydroxide. The resulting solid was isolated by filtration, washed with water and then air dried to provide 11.8 g of crude product as a tan powder. This material was recrystallized from ethyl acetate/methanol to provide 4.9 g of 2-pyrrolidino-1H-benzimidazole. Analysis: Calculated for C11H13N3: % C, 70.56; % H, 7.00; % N, 22.44. Found: % C, 70.13; % H, 7.05; % N, 22.70.

Workup

  1. customthe solvent was evaporated
  2. additionThe resulting residue was mixed with water
  3. customThe resulting solid was isolated by filtration
  4. washwashed with water
  5. customair dried
  6. customto provide 11.8 g of crude product as a tan powder
  7. customThis material was recrystallized from ethyl acetate/methanol

Sources & evidence

ORD record
ord-72dc2ca90ac5467e9e4f90f2467f17ca
Source dataset
uspto-grants-2004_06
Patent number
US06756382B2

Reaction notes

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