Iodoethane → HCID 11268950, compound

HRID 643257Notes

Reaction equation

HRID 643257 reaction equation
[CH3:1][C:2]12[CH2:22][CH:6]([N:7]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[CH:13][CH:12]=3)=[O:10])[CH2:8]1)[CH2:5][C:4]([CH3:24])([CH3:23])[CH2:3]2.[H-].[Na+].[CH2:27](I)[CH3:28]>CN(C=O)C>[CH2:27]([N:17]([C:14]1[CH:15]=[CH:16][C:11]([C:9]([N:7]2[CH2:8][C:2]3([CH3:1])[CH2:22][CH:6]2[CH2:5][C:4]([CH3:24])([CH3:23])[CH2:3]3)=[O:10])=[CH:12][CH:13]=1)[S:18]([CH3:21])(=[O:19])=[O:20])[CH3:28]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 11337064HCID 11337064, compound

Product 1

HCID 11268950HCID 11268950, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-methanesulfonamide (300 mg, 0.86 mmol) in dry DMF (25 ml) was added sodium hydride (42 mg, 1.73 mmol in 60% mineral oil) and the mixture was stirred for 1 hr. Ethyl iodide (83 μl, 1.03 mmol) was added and the stirring was continued for an additional 16 hrs. The reaction was quenched by addition of water (25 ml) and extracted with diethyl ether (2×50 ml). The combined organic phases were dried (Na2SO4), filtered and evaporated in vacuo. 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 a slowly crystallizing oil which was suspended in diethyl ether and the solid filtered off affording 140 mg (43%) of the title compound as a solid.

Workup

  1. waitthe stirring was continued for an additional 16 hrs
  2. customThe reaction was quenched by addition of water (25 ml)
  3. extractionextracted with diethyl ether (2×50 ml)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography (silica gel)
  8. customPure fractions were collected
  9. customevaporated to dryness
  10. customaffording
  11. customa slowly crystallizing oil which
  12. filtrationthe solid filtered off

Sources & evidence

ORD record
ord-44fd95690ea04bf99076336bef6f6d1b
Source dataset
uspto-grants-2010_04
Patent number
US07700583B2

Reaction notes

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