Methyl iodide → HCID 86719541, compound

HRID 2208725Notes

Reaction equation

HRID 2208725 reaction equation
[CH:1]1([NH:6][C:7]2[C:8]([CH3:17])=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([O:12][CH3:13])=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:18](=O)([O-])[O-].[Cs+].[Cs+].CI>C(#N)C>[CH:1]1([N:6]([CH3:18])[C:7]2[C:8]([CH3:17])=[C:9]([CH:14]=[CH:15][CH:16]=2)[C:10]([O:12][CH3:13])=[O:11])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 43714396HCID 43714396, compound

Product 1

HCID 86719541HCID 86719541, compoundYield 85.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of methyl 3-(cyclopentylamino)-2-methylbenzoate (2.2 g, 9.44 mmol) in acetonitrile (20 mL) was added cesium carbonate (6.13 g, 18.8 mmol) and methyl iodide (6.7 g, 47.2 mmol). The resulting mixture was heated at 80° C. for 12 h. On completion, the mixture was cooled to room temperature and filtered, washing with ethyl acetate. The filtrate was concentrated and then purified by column chromatography to afford methyl 3-(cyclopentyl(methyl)amino)-2-methylbenzoate (2 g, 85%).

Workup

  1. temperatureOn completion, the mixture was cooled to room temperature
  2. filtrationfiltered
  3. washwashing with ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-e44dc7394a7041e0b27b2a4ad4cd0880
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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