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

HRID 1910637Notes

Reaction equation

HRID 1910637 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[N+:24]([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[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH:15]=[CH:14][C:13]=2[N+:24]([O-:26])=[O:25])[CH3:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58707285N-(1-(3,5-dichlorophenyl)ethyl)-2-nitro-5-(piperazin-1-yl)benzeneamine

Product 1

HCID 67147381N-(1-(3,5-Dichlorophenyl)ethyl)-2-nitro 5-(piperazin-1-yl)-benzeneamine hydrochlorideYield 39%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(1-(3,5-dichlorophenyl)ethyl)-2-nitro-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 39% 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 C18H20Cl2N4O2.HCl: 431.74; Observed: 396.4 (M++1 corresponding to its free base).

Workup

  1. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-7a9ddd72dc1d4487959eb7610e9697ff
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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