Hydrochloric Acid → 4-(7-chloro-2H-benzopyran-3-sulfonyl)-1-(4-methoxycarbonylpiperidin-4-ylmethyl)-2-piperazinone hydrochloride

HRID 1840560Notes

Reaction equation

HRID 1840560 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH2:18][N:19]2[CH2:24][CH2:23][N:22]([S:25]([C:28]3[CH2:29][O:30][C:31]4[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:32]=4[CH:33]=3)(=[O:27])=[O:26])[CH2:21][C:20]2=[O:39])([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>C(OCC)(=O)C.CO>[ClH:38].[Cl:38][C:36]1[CH:35]=[CH:34][C:32]2[CH:33]=[C:28]([S:25]([N:22]3[CH2:23][CH2:24][N:19]([CH2:18][C:11]4([C:14]([O:16][CH3:17])=[O:15])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]4)[C:20](=[O:39])[CH2:21]3)(=[O:27])=[O:26])[CH2:29][O:30][C:31]=2[CH:37]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 234476081-[1-(tert-butoxycarbonyl)-4-methoxycarbonylpiperidin-4-ylmethyl]-4-(7-chloro-2H-benzopyran-3-sulfonyl)-2-piperazinone

Product 1

HCID 234475944-(7-chloro-2H-benzopyran-3-sulfonyl)-1-(4-methoxycarbonylpiperidin-4-ylmethyl)-2-piperazinone hydrochlorideYield 196.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1-[1-(tert-butoxycarbonyl)-4-methoxycarbonylpiperidin-4-ylmethyl]-4-(7-chloro-2H-benzopyran-3-sulfonyl)-2-piperazinone (260 mg) was added 4N hydrochloric acid in ethyl acetate (10 ml) and methanol (4 ml), and the mixture was stirred at room temperature for 30 minutes. The reaction solution was concentrated to give colorless solid of 4-(7-chloro-2H-benzopyran-3-sulfonyl)-1-(4-methoxycarbonylpiperidin-4-ylmethyl)-2-piperazinone hydrochloride (228 mg). A solution of 4-(7-chloro-2H-benzopyran-3-sulfonyl)-1-(4-methoxycarbonylpiperidin-4-ylmethyl)-2-piperazinone hydrochloride (228 mg), chloropyridine hydrochloride (80 mg) and triethylamine (225 mg) in ethanol (14 ml) was allowed to react in a sealed tube at 150% 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 of the title compound (126 mg).

Workup

  1. concentrationThe reaction solution was concentrated

Sources & evidence

ORD record
ord-f6d95f300f9d404e81b05fe4632c2ca1
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

Loading…