Hydrochloric Acid → N-(1-(3,5-Dichlorophenyl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzeneamine hydrochloride

HRID 1910586Notes

Reaction equation

HRID 1910586 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:11][C:12]2[CH:17]=[C:16]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH:15]=[CH:14][C:13]=2[S:24]([CH3:27])(=[O:26])=[O:25])[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.Cl>ClCCl.C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:11][C:12]2[CH:17]=[C:16]([N:18]3[CH2:19][CH2:20][NH:21][CH2:22][CH2:23]3)[CH:15]=[CH:14][C:13]=2[S:24]([CH3:27])(=[O:25])=[O:26])[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58707288N-(1-(3,5-dichlorophenyl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzeneamine

Product 1

HCID 67147528N-(1-(3,5-Dichlorophenyl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzeneamine hydrochlorideYield 95%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1-(3,5-dichlorophenyl)ethyl)-2-(methylsulfonyl)-5-(piperazin-1-yl)benzeneamine (0.09 mmol) in dichloromethane (2.0 mL) was added a saturated solution of HCl in diethyl ether (15 mL). The reaction mixture was stirred for 2 h. The solvent was removed by rotary evaporation to afford the title compound in 95% yield. 1H NMR (400 MHz, CD3OD): δ 7.67 (d, 1H), 7.37 (s, 2H), 7.35 (s, 1H), 6.41 (d, 1H), 5.84 (s, 1H), 4.79 (m, 1H), 3.57 (m, 4H), 3.25 (m, 4H), 1.61 (d, 3H); MS (ESI) m/z: Calculated for C19H24Cl3N3O2S: 464.8; Observed: 465.5 (M++1).

Workup

  1. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-c52ff94b70aa44e5a3dca24634195e08
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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