Methyl iodide → HCID 68783444, compound

HRID 2063930Notes

Reaction equation

HRID 2063930 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1.[OH-].[K+].[CH3:25]I>CC(C)=O>[CH3:25][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 54672426tert-butyl 4-(1H-benzo[d]iMidazol-2-yl)piperidine-1-carboxylate

Product 1

HCID 68783444HCID 68783444, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The tert-butyl 4-(1H-benzimidazol-2-yl)piperidine-1-carboxylate (50.0 mg, 0.166 mmol) was dissolved in 2 mL of acetone with freshly ground potassium hydroxide (46.4 mg, 0.830 mmol). The mixture was stirred for 10 minutes at ambient temperature, and then methyl iodide (11.4 μL, 0.183 mmol) was added. After 10 minutes, the reaction was quenched by adding saturated aqueous ammonium chloride solution (10 mL). The sample was diluted with EtOAc (3×30 mL), washed with water (2×20 mL), and washed with brine (2×20 mL). The organic layer was dried over sodium sulfate, filtered, concentrated to give tert-butyl 4-(1-methyl-1H-benzimidazol-2-yl)piperidine-1-carboxylate.

Workup

  1. waitAfter 10 minutes
  2. customthe reaction was quenched
  3. additionby adding saturated aqueous ammonium chloride solution (10 mL)
  4. additionThe sample was diluted with EtOAc (3×30 mL)
  5. washwashed with water (2×20 mL)
  6. washwashed with brine (2×20 mL)
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-73d5cce406944c3ca0b4012906135592
Source dataset
uspto-grants-2012_10
Patent number
US08288409B2

Reaction notes

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