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Propargyl bromide → 1-[1-(1-methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]-3-(2-propinyl)-1,3-dihydro-2H-benzimidazol-2-one

HRID 47519
Notes
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Reaction equation

HRID 47519 reaction equation
[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[NH:19][C:18]3=[O:26])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4].[H-].[Na+].[CH2:29](Br)[C:30]#[CH:31].C(=O)(O)[O-].[Na+]>CN(C)C=O.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[N:19]([CH2:31][C:30]#[CH:29])[C:18]3=[O:26])[CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 516892Sodium Bicarbonate2×HCID 227452181-[1-(1-methoxycarbonylpiperidin-4-yl)piperidin-4-yl]-1,3-dihydro-2H-benzimidazol-2-one

Product 1

HCID 121276521-[1-(1-methoxycarbonylpiperidin-4-yl)-piperidin-4-yl]-3-(2-propinyl)-1,3-dihydro-2H-benzimidazol-2-one

Reagents, catalysts & solvents

2
HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

1-[1-(1-Methoxycarbonylpiperidin-4-yl)piperidin-4-yl]-1,3-di-hydro-2H-benzimidazol-2-one (28 mg) as synthesized by the method of Referential Example 1 was dissolved in 5 ml of dimethylformamide, and to which 2.0 mg of sodium hydride was added under cooling with ice, followed by 30 minutes' stirring. Ten(10) mg of propargyl bromide was added to the reaction liquid which was stirred for further 3 hours at room temperature. After adding saturated aqueous sodium bicarbonate solution and concentrating the reaction liquid, the resulting residue was distributed between saturated aqueous sodium bicarbonate solution and chloroform. The organic layer was dried over anhydrous sodium sulfate, concentrated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol=20/1). Thus 11.3 mg of the title compound was obtained as a colorless oil.

Workup

  1. temperatureunder cooling with ice
  2. stirringwas stirred for further 3 hours at room temperature
  3. concentrationconcentrating
  4. customthe reaction liquid
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-dd75cdfd697344ccab8f96882d9483e6
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06699880B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes