Piperazine → N-(2-methoxyphenyl)-4-(piperazinyl)-3-nitrobenzenesulfonamide

HRID 230541

Reaction equation

HRID 230541 reaction equation
ClC1C=CC(S(Cl)(=O)=O)=CC=1[N+]([O-])=O.COC1C=CC=CC=1N.Cl[C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[O:41][CH3:42])(=[O:33])=[O:32])=[CH:27][C:26]=1[N+:43]([O-:45])=[O:44].[NH:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1>N1C=CC=CC=1>[CH3:42][O:41][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[NH:34][S:31]([C:28]1[CH:29]=[CH:30][C:25]([N:46]2[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]2)=[C:26]([N+:43]([O-:45])=[O:44])[CH:27]=1)(=[O:33])=[O:32]

Participants

6

Reactant 4

HCID 4837PiperazineHCID 70002-MethoxyanilineHCID 7323Benzenesulfonyl chloride, 4-chloro-3-nitro-HCID 28876834-chloro-N-(2-methoxyphenyl)-3-nitrobenzenesulfonamide

Product 1

HCID 22272580N-(2-methoxyphenyl)-4-(piperazinyl)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The compound was prepared from 4-chloro-3-nitrobenzenesulfonyl chloride (1 g, 3.9 mmol), 2-methoxyaniline (0.53 mL, 4.7 mmol) and pyridine (1.6 mL) in CH2CL2 (2 mL). 4-Chloro-N-(2-methoxyphenyl)-3-nitrobenzenesulfonamide (0.345 g) was reacted with piperazine (0.111 g) to afford N-(2-methoxyphenyl)-4-(piperazinyl)-3-nitrobenzenesulfonamide. This was then treated with Raney-Ni and hydrazine monohydrate. The final product was isolated as its HCl salt. 1H NMR (DMSO-d6) δ 7.18-7.20 (m, 1H), 7.08-7.10 (m, 2H), 6.93-6.96 (m, 1H), 6.91-6.93 (m, 2H); 6.84 (dt, 1H), 3.56 (s, 3H), 3.22-3.27 (m, 4H), 3.00-3.02 (m, 4H); MS (posESI) m/z=362.1 (M+H+).

Sources & evidence

ORD record
ord-c7bd99f4cebb4989bdf507cdd70e54b1
Source dataset
uspto-grants-2009_07
Patent number
US07566715B2

Linked notes

Loading…