Methanesulfonyl chloride → N-Methyl-N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-methane-sulfonamide

HRID 643256Notes

Reaction equation

HRID 643256 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([N:11]2[CH2:17][C:16]3([CH3:19])[CH2:18][CH:12]2[CH2:13][C:14]([CH3:21])([CH3:20])[CH2:15]3)=[O:10])=[CH:5][CH:4]=1.[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:1][N:2]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([N:11]2[CH2:17][C:16]3([CH3:19])[CH2:18][CH:12]2[CH2:13][C:14]([CH3:21])([CH3:20])[CH2:15]3)=[O:10])=[CH:5][CH:4]=1)[S:23]([CH3:22])(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 11414957(4-Methylamino-phenyl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone

Product 1

HCID 11439934N-Methyl-N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-methane-sulfonamideYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (4-methylamino-phenyl)-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone (0.7 g, 2.44 mmol), DCM (40 ml) and TEA (0.7 ml, 4.89 mmol) was added methansulfonyl chloride (285 μl, 3.67 mmol). The resulting mixture was stirred for 4 hrs. at room temperature followed by evaporation of the volatiles in vacuo. The residue was dissolved in diethyl ether (10 ml), washed with water (2×10 ml) evaporated and the residue purified by column chromatography (silica gel) using a mixture of EtOAc-Heptane (1:1) as eluent. Pure fractions were collected and evaporated to dryness. The residue was crystallized from diethyl ether (10 ml), filtered off and dried in vacuo at 50° C. affording 0.45 g (51%) of the title compound as a solid.

Workup

  1. customat room temperature followed by evaporation of the volatiles in vacuo
  2. dissolutionThe residue was dissolved in diethyl ether (10 ml)
  3. washwashed with water (2×10 ml)
  4. customevaporated
  5. customthe residue purified by column chromatography (silica gel)
  6. additiona mixture of EtOAc-Heptane (1:1) as eluent
  7. customPure fractions were collected
  8. customevaporated to dryness
  9. customThe residue was crystallized from diethyl ether (10 ml)
  10. filtrationfiltered off
  11. customdried in vacuo at 50° C.

Sources & evidence

ORD record
ord-37d7baaefb8c43928d0389d44e5465fe
Source dataset
uspto-grants-2010_04
Patent number
US07700583B2

Reaction notes

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