Potassium Iodide → 6-Methanesulfonamido-2-(1-[4-methanesulfonamidophenethyl]-4-piperidyl)indan-1-one hydrochloride

HRID 1586716Notes

Reaction equation

HRID 1586716 reaction equation
[ClH:1].[CH3:2][S:3]([NH:6][C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][CH:12]([CH:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:13]2=[O:16])=[CH:9][CH:8]=1)(=[O:5])=[O:4].C(=O)(O)[O-].[Na+].S(O[CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([NH:41][S:42]([CH3:45])(=[O:44])=[O:43])=[CH:37][CH:36]=1)(=O)(=O)C.[I-].[K+]>C(OCC)(=O)C.C(#N)C>[ClH:1].[CH3:2][S:3]([NH:6][C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][CH:12]([CH:17]3[CH2:22][CH2:21][N:20]([CH2:33][CH2:34][C:35]4[CH:36]=[CH:37][C:38]([NH:41][S:42]([CH3:45])(=[O:43])=[O:44])=[CH:39][CH:40]=4)[CH2:19][CH2:18]3)[C:13]2=[O:16])=[CH:9][CH:8]=1)(=[O:4])=[O:5]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 149859624-Methanesulphonamidophenethyl mesylateHCID 197591836-Methanesulfonamido-2-(4-piperidyl)indan-1-one hydrochloride

Product 1

HCID 197592026-Methanesulfonamido-2-(1-[4-methanesulfonamidophenethyl]-4-piperidyl)indan-1-one hydrochlorideYield 86%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.100 g (0.00029 mol) of 6-methanesulfonamido-2-(4-piperidyl)indan-1-one hydrochloride, 0.073 g (0.00087 mol) of sodium bicarbonate, 0.128 g (0.00044 mol) of 4-methanesulfonamidophenethyl alcohol mesylate, 15 mg of potassium iodide, and 10 mL of acetonitrile was stirred and refluxed for 32 hours. The cooled solution, transferred to a separatory funnel using 25 mL of ethyl acetate, was washed with water and then with brine. The organic phase was extracted with three 4 mL portions of 1N HCl. The combined acid extracts were made basic by addition of solid sodium bicarbonate, and the basic phase was extracted with three 30 mL portions of ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and the solvent was removed under reduced pressure to afford 0.125 g (86%) of product. A hydrochloride salt was prepared in methanol; mp 130°-135° (foams).

Workup

  1. temperaturerefluxed for 32 hours
  2. customThe cooled solution, transferred to a separatory funnel
  3. washwas washed with water
  4. extractionThe organic phase was extracted with three 4 mL portions of 1N HCl
  5. additionThe combined acid extracts were made basic by addition of solid sodium bicarbonate
  6. extractionthe basic phase was extracted with three 30 mL portions of ethyl acetate
  7. dry with materialThe combined organic extracts were dried over magnesium sulfate
  8. filtrationfiltered
  9. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-3e08eabb32d644c3a6bf99fa18c00ce2
Source dataset
uspto-grants-1993_06
Patent number
US05215989

Reaction notes

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