Sodium Bicarbonate → 4-(7-chloro-2H-benzopyran-3-sulfonyl)-1-[1-(4-pyridyl)piperidin-4-ylmethyl]-2-piperazinone

HRID 1840568Notes

Reaction equation

HRID 1840568 reaction equation
C(=O)(O)[O-].[Na+].Cl.[Cl:7][C:8]1[CH:34]=[CH:33][C:11]2[CH:12]=[C:13]([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])[CH2:14][O:15][C:10]=2[CH:9]=1.Cl.Cl[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=1>>[Cl:7][C:8]1[CH:34]=[CH:33][C:11]2[CH:12]=[C:13]([S:16]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][CH:26]4[CH2:27][CH2:28][N:29]([C:41]5[CH:40]=[CH:39][N:38]=[CH:37][CH:42]=5)[CH2:30][CH2:31]4)[C:21](=[O:32])[CH2:20]3)(=[O:17])=[O:18])[CH2:14][O:15][C:10]=2[CH:9]=1

Participants

4

Reactant 3

HCID 516892Sodium BicarbonateHCID 156199202-Chloropyridine--hydrogen chloride (1/1)HCID 234473484-(7-chloro-2H-benzopyran-3-sulfonyl)-1-(piperidin-4-ylmethyl)-2-piperazinone hydrochloride

Product 1

HCID 234473644-(7-chloro-2H-benzopyran-3-sulfonyl)-1-[1-(4-pyridyl)piperidin-4-ylmethyl]-2-piperazinoneYield 39.9%

Procedure

To sodium bicarbonate solution were added 4-(7-chloro-2H-benzopyran-3-sulfonyl)-1-(piperidin-4-ylmethyl)-2-piperazinone hydrochloride (1.4 g) and chloropyridine hydrochloride (1.02 g), and the mixture was extracted with dichloromethane (twice), dried and concentrated. To the residue was added isoamylalcohol (50 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 1 N sodium hydroxide solution, dried and concentrated, and the residue was purified with silica gel column chromatography (dichloromethane: methanol containing 10% ammonia solution=20: 1) to give colorless solid 4-(7-chloro-2H-benzopyran-3-sulfonyl)-1-[1-(4-pyridyl)piperidin-4-ylmethyl]-2-piperazinone (608 mg).

Workup

  1. extractionthe mixture was extracted with dichloromethane (twice),
  2. customdried
  3. concentrationconcentrated
  4. additionTo the residue was added isoamylalcohol (50 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 1 N sodium hydroxide solution
  9. customdried
  10. concentrationconcentrated
  11. customthe residue was purified with silica gel column chromatography (dichloromethane: methanol containing 10% ammonia solution=20: 1)

Sources & evidence

ORD record
ord-26b36f0ec78b493c830a6fa7efb6094c
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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