Methyl iodide → HCID 11338297, compound

HRID 643259Notes

Reaction equation

HRID 643259 reaction equation
[CH3:1][C:2]12[CH2:26][CH:6]([N:7]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:25])[C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)=[CH:13][CH:12]=3)=[O:10])[CH2:8]1)[CH2:5][C:4]([CH3:28])([CH3:27])[CH2:3]2.[H-].[Na+].[CH3:31]I>C1COCC1>[CH3:31][N:17]([C:14]1[CH:15]=[CH:16][C:11]([C:9]([N:7]2[CH2:8][C:2]3([CH3:1])[CH2:26][CH:6]2[CH2:5][C:4]([CH3:28])([CH3:27])[CH2:3]3)=[O:10])=[CH:12][CH:13]=1)[C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11451692HCID 11451692, compound

Product 1

HCID 11338297HCID 11338297, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-benzamide (500 mg, 1.33 mmol) in dry THF (40 ml) was added sodium hydride (64 mg, 1.594 mmol in 60% mineral oil) and the mixture was stirred for 30 min. Methyl iodide (99 μl, 1.594 mmol) was added and the stirring was continued for an additional 2 hrs. The volatiles were evaporated in vacuo and the residue was purified by column chromatography (silica gel) using EtOAc-Heptane (1:1) as eluent. Pure fractions were collected and evaporated to dryness affording 300 mg (58%) of the title compound as a solid.

Workup

  1. waitthe stirring was continued for an additional 2 hrs
  2. customThe volatiles were evaporated in vacuo
  3. customthe residue was purified by column chromatography (silica gel)
  4. customPure fractions were collected
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-5ec8abb81e0a473c8c52536c2e2a5ae3
Source dataset
uspto-grants-2010_04
Patent number
US07700583B2

Reaction notes

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