Methyl iodide → HCID 20203540, compound

HRID 978718Notes

Reaction equation

HRID 978718 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[CH2:11][CH2:12][CH2:13][CH:14]([NH:15][CH:16]=[O:17])[C:3]=12.[H-].[Na+].[CH3:20]I>CN(C)C=O>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]2[CH2:11][CH2:12][CH2:13][CH:14]([N:15]([CH3:20])[CH:16]=[O:17])[C:3]=12

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13749193HCID 13749193, compound

Product 1

HCID 20203540HCID 20203540, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A solution of N-(6,7,8,9-tetrahydro-10-methylpyrido[1,2-a]indol-9-yl)formamide (7.4 g, 32.4 mmol) in dimethylformamide (90 mL) was added dropwise at 25° C. to a suspension of sodium hydride (1.78 g, 37 mmol, ~50% suspension in mineral oil) in the same solvent (90 mL). The reaction mixture was stirred at 25° C. for 2 hours under exclusion of moisture. Methyl iodide (5.1 g, 35.6 mmol) was added and the mixture stirred at 25° C. overnight. The solvent was evaporated in vacuo and the residue partitioned between water (100 mL) and chloroform (150 mL). The organic layer was separated, dried over MgSO4, filtered, and evaporated to afford 7.85 g (100%) of the title compound as an amber oil.

Workup

  1. stirringthe mixture stirred at 25° C. overnight
  2. customThe solvent was evaporated in vacuo
  3. customthe residue partitioned between water (100 mL) and chloroform (150 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-6cbe8099b6db4cf3a2e94ea810f5d383
Source dataset
uspto-grants-1987_05
Patent number
US04665183

Reaction notes

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