Potassium Iodide → N-[2-[1-[2-(5-Benzofurazanyl)ethyl]-4-piperidinyl]-2,3-dihydro-3-oxo-1H-inden-5-yl]methanesulfonamide

HRID 1195686Notes

Reaction equation

HRID 1195686 reaction equation
Cl.[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].Br[CH2:24][CH2:25][C:26]1[CH:27]=[CH:28][C:29]2[C:30]([CH:34]=1)=[N:31][O:32][N:33]=2.C(=O)(O)[O-].[Na+].[I-].[K+]>C(#N)C>[N:33]1[O:32][N:31]=[C:30]2[CH:34]=[C:26]([CH2:25][CH2:24][N:20]3[CH2:21][CH2:22][CH:17]([CH:12]4[C:13](=[O:16])[C:14]5[C:10](=[CH:9][CH:8]=[C:7]([NH:6][S:3]([CH3:2])(=[O:4])=[O:5])[CH:15]=5)[CH2:11]4)[CH2:18][CH2:19]3)[CH:27]=[CH:28][C:29]=12

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 516892Sodium BicarbonateHCID 117758995-(2-Bromoethyl)benzofurazanHCID 197591836-Methanesulfonamido-2-(4-piperidyl)indan-1-one hydrochloride

Product 1

HCID 54107427N-[2-[1-[2-(5-Benzofurazanyl)ethyl]-4-piperidinyl]-2,3-dihydro-3-oxo-1H-inden-5-yl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In the manner described in Example 14, 6-methanesulfonamido-2-(4-piperidyl)-indan-1-one hydrochloride (0.20 g, 0.58 mmol), 5-(2-bromoethyl)benzofurazan (0.395 g, 1.74 mmol), sodium bicarbonate (0.146 g, 1.74 mmol) and potassium iodide (20 mg), in 20 mL of acetonitrile were heated under reflux for 30 hours. After purification by flask column chromatography on silica gel eluting with 5% methanol in chloroform saturated with ammonia (gas), and treatment with ethanol HCl, crystallization from methanol gave the title compound as a white solid, mp 214°-217° C.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 30 hours
  3. customAfter purification by flask column chromatography on silica gel eluting with 5% methanol in chloroform saturated with ammonia (gas), and treatment
  4. customwith ethanol HCl, crystallization from methanol

Sources & evidence

ORD record
ord-55a7a0ef3bdc4910bf893274e3abe5b0
Source dataset
uspto-grants-1992_05
Patent number
US05112824

Reaction notes

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