Triethylamine → HCID 9846314, compound

HRID 47530Notes

Reaction equation

HRID 47530 reaction equation
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[NH:17][C:16]3=[O:24])[CH2:11][CH2:10]2)[CH2:5][CH2:4]1.Cl[C:26]([O:28][CH2:29][CH3:30])=[O:27].C(N([CH2:36][CH3:37])CC)C.[C:38](=O)([O-:40])[OH:39].[Na+]>C(Cl)(Cl)Cl>[CH2:29]([O:28][C:26]([N:3]1[CH2:4][CH2:5][CH:6]([N:9]2[CH2:10][CH2:11][CH:12]([N:15]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=4[N:17]([C:38]([O:40][CH2:36][CH3:37])=[O:39])[C:16]3=[O:24])[CH2:13][CH2:14]2)[CH2:7][CH2:8]1)=[O:27])[CH3:30]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 227452031-[1-(piperidin-4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one dihydrochloride

Product 1

HCID 9846314HCID 9846314, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1-[1-(Piperidin-4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one-dihydrochloride (37.3 mg) was dissolved in 3 ml of chloroform, and to which 21 μl of ethyl chloroformate and 84 μl of triethylamine were successively added under cooling with ice, followed by overnight stirring at room temperature. To the reaction liquid saturated aqueous sodium hydrogencarbonate solution was added and extracted with chloroform. The organic layer was washed with saturated. brine, dried over anhydrous sodium sulfate and then the solvent was distilled off. The resulting residue was purified by silica gel column chromatography (chloroform/methanol=10/1) to provide 41.7 mg of the title compound as a colorless oil.

Workup

  1. temperatureunder cooling with ice
  2. additionwas added
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with saturated
  5. dry with materialbrine, dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off
  7. customThe resulting residue was purified by silica gel column chromatography (chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-4cff432082f54af1baff8ac907c5a989
Source dataset
uspto-grants-2004_03
Patent number
US06699880B1

Reaction notes

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