Sodium Bicarbonate → 4-(5-Chlorobenzofuran-2-sulfonyl)-1-[1-(4-pyridyl)piperidin-4-ylmethyl]-2-piperazinone

HRID 2186161Notes

Reaction equation

HRID 2186161 reaction equation
C(=O)(O)[O-].[Na+].Cl.[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([S:16]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[C:21](=[O:32])[CH2:20]3)(=[O:18])=[O:17])=[CH:13][C:12]=2[CH:33]=1.Cl.Cl[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1>>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([S:16]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH:26]4[CH2:27][CH2:28][N:29]([C:40]5[CH:39]=[CH:38][N:37]=[CH:36][CH:41]=5)[CH2:30][CH2:31]4)[C:21](=[O:32])[CH2:20]3)(=[O:18])=[O:17])=[CH:13][C:12]=2[CH:33]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 156199202-Chloropyridine--hydrogen chloride (1/1)HCID 234473124-(5-Chlorobenzofuran-2-sulfonyl)-1-(piperidin-4-ylmethyl)-2-piperazinone hydrochloride

Product 1

HCID 234473164-(5-Chlorobenzofuran-2-sulfonyl)-1-[1-(4-pyridyl)piperidin-4-ylmethyl]-2-piperazinoneYield 37.1%

Procedure

To sodium bicarbonate solution were added 4-(5-chlorobenzofuran-2-sulfonyl)-1-(piperidin-4-ylmethyl)-2-piperazinone hydrochloride (215 mg) and chloropyridine hydrochloride (144 mg), and the mixture was extracted with dichloromethane (twice), dried and concentrated. To the residue was added isoamylalcohol (15 ml), and the mixture was allowed to react at 130° C. for 15 hours. The reaction solution was concentrated, and the residue was dissolved in dichloromethane. The solution was washed with 1N sodium hydroxide solution, dried and concentrated, and the residue was purified with silica gel column chromatography (dichloromethane:methanol containing 10% ammonia solution=15:1) to give colorless solid of 4-(5-chlorobenzofuran-2-sulfonyl)-1-[1-(4-pyridyl)piperidin-4-ylmethyl]-2-piperazinone (87 mg), which was treated with hydrochloric acid to give colorless solid of the title compound (80 mg) as hydrochloride salt.

Workup

  1. extractionthe mixture was extracted with dichloromethane (twice),
  2. customdried
  3. concentrationconcentrated
  4. additionTo the residue was added isoamylalcohol (15 ml)
  5. customto react at 130° C. for 15 hours
  6. concentrationThe reaction solution was concentrated
  7. dissolutionthe residue was dissolved in dichloromethane
  8. washThe solution was washed with 1N sodium hydroxide solution
  9. customdried
  10. concentrationconcentrated
  11. customthe residue was purified with silica gel column chromatography (dichloromethane:methanol containing 10% ammonia solution=15:1)

Sources & evidence

ORD record
ord-909a15a3cc644e31bd5b3ce32a39f61e
Source dataset
uspto-grants-2002_06
Patent number
US06403595B1

Reaction notes

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