1,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one → HCID 86589516, compound

HRID 1295768Notes

Reaction equation

HRID 1295768 reaction equation
[O:1]=[C:2]1[N:6]([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[C:5]2[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=2[NH:3]1.[CH:17]1[CH:22]=[CH:21][C:20]([O:23][C:24](OC2C=CC=CC=2)=[N:25][C:26]#[N:27])=[CH:19][CH:18]=1>C(#N)C>[C:20]1([O:23][C:24]([N:10]2[CH2:9][CH2:8][CH:7]([N:6]3[C:5]4[CH:13]=[CH:14][CH:15]=[CH:16][C:4]=4[NH:3][C:2]3=[O:1])[CH2:12][CH2:11]2)=[N:25][C:26]#[N:27])[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 688090Diphenyl N-Cyanocarbonimidate

Product 1

HCID 86589516HCID 86589516, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4-(2-keto-1-benzimidazolinyl)piperidine (1.3 g; 5.98 mmol) in acetonitrile was added diphenyl N-cyanocarbonimidate (1.56 g; 6.55 mmol; 1.1 equiv). The reaction mixture was stirred at 60° C. for 48 h under nitrogen atmosphere and then concentrated under reduced pressure. The crude product was suspended in ethyl acetate (50 mL) and a saturated aqueous solution of sodium bicarbonate (50 mL) and stirred overnight at room temperature. The solid was collected by filtration and dried to give N-cyano-4-(2-oxo-2,3-dihydro-benzoimidazol-1-yl)-piperidine-1-carboximidic acid phenyl ester (1.85 g; 85%) as a white solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. stirringa saturated aqueous solution of sodium bicarbonate (50 mL) and stirred overnight at room temperature
  3. filtrationThe solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-608073f1edf74501811ff0aa1a803ba0
Source dataset
uspto-grants-2007_07
Patent number
US07244744B2

Reaction notes

Loading…