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

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

Reactant 3

HCID 516892Sodium Bicarbonate

HCID 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 1N 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).