Cyclopentanecarboxylic acid, 2-oxo-, methyl ester → HCID 178509355, compound

HRID 70795Notes

Reaction equation

HRID 70795 reaction equation
[NH:1]1[C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=2[N:3]=[C:2]1[CH2:10][C:11]#[N:12].O=[C:14]1[CH2:18][CH2:17][CH2:16][CH:15]1[C:19](OC)=[O:20].C([O-])(=O)C.[NH4+]>O>[OH:20][C:19]1[N:3]2[C:2](=[N:1][C:5]3[CH2:6][CH2:7][CH2:8][CH2:9][C:4]=32)[C:10]([C:11]#[N:12])=[C:14]2[CH2:18][CH2:17][CH2:16][C:15]=12

Participants

5

Reactant 3

HCID 66328Cyclopentanecarboxylic acid, 2-oxo-, methyl esterHCID 517165Ammonium AcetateHCID 70170207HCID 70170207, compound

Product 1

HCID 178509355HCID 178509355, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4,5,6,7-tetrahydro-1H-benzimidazol-2-yl acetonitrile (8.5 g), methyl 2-oxocyclopentanecarboxylate (7.5 g) and ammonium acetate (20.3 g) was stirred at 140° C. for 2 hours. The reaction mixture was cooled to room temperature, water was added, and extraction was performed with chloroform. The organic layer was washed with a saturated brine, dried over anhydrous sodium sulfate, and concentrated reduced pressure. The residue was solidified using hexane/EtOAc to obtain 11-hydroxy-2,3,6,7,8,9-hexahydro-1H-cyclopenta[4,5]pyrido[1,2-a]benzimidazole-4-carbonitrile (2.56 g).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextraction
  3. washThe organic layer was washed with a saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated reduced pressure

Sources & evidence

ORD record
ord-15fc00a111be4bcb8145085f2c49b920
Source dataset
uspto-grants-2014_09
Patent number
US08822688B2

Reaction notes

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