HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Methyl iodide → (R)-1-[1-(acenaphthen-1-yl)piperidin-4-yl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

HRID 331251
Notes
Print preview

Reaction equation

HRID 331251 reaction equation
[C@H:1]1([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[NH:21][C:20]3=[O:28])[CH2:15][CH2:14]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1.[H-].[Na+].[CH3:31]I.[Cl-].[NH4+]>CN(C=O)C>[C@H:1]1([N:13]2[CH2:14][CH2:15][CH:16]([N:19]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[N:21]([CH3:31])[C:20]3=[O:28])[CH2:17][CH2:18]2)[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH:6]=[CH:5][CH:4]=[C:3]3[CH2:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59322973HCID 59322973, compound

Product 1

HCID 59322980(R)-1-[1-(acenaphthen-1-yl)piperidin-4-yl]-3-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneYield 71.6%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

(R)-1-[1-(Acenaphthen-1-yl)piperidin-4-yl]-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (0.78 g) was dissolved in DMF (20 ml), 60% sodium hydride (90 mg) was added, and the suspension was stirred for 20 min. Then, methyl iodide (340 mg) was added, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was poured into saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over magnesium sulfate, and concentrated. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to give the title compound (0.58 g) as a yellow powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-681846dd40624732ac9e7453adbaef42
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08877779B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes