Hydrochloric Acid → N-(1-(3-Chlorophenyl)ethyl)-2-nitro-5-(piperazin-1-yl)benzenamine hydrochloride

HRID 1910533Notes

Reaction equation

HRID 1910533 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:10][C:11]2[CH:12]=[C:13]([N:20]3[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]3)[CH:14]=[CH:15][C:16]=2[N+:17]([O-:19])=[O:18])[CH3:9])[CH:5]=[CH:6][CH:7]=1.Cl>ClCCl.C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:10][C:11]2[CH:12]=[C:13]([N:20]3[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]3)[CH:14]=[CH:15][C:16]=2[N+:17]([O-:19])=[O:18])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58707320t-Butyl 4-(3-(1-(3-chlorophenyl)ethylamino)-4-nitrophenyl)piperazine-1-carboxylate

Product 1

HCID 67147352N-(1-(3-Chlorophenyl)ethyl)-2-nitro-5-(piperazin-1-yl)benzenamine hydrochlorideYield 139%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl 4-(3-(1-(3-chlorophenyl)ethylamino)-4-nitrophenyl)piperazine-1-carboxylate (97 mg, 0.21 mmol) in dry dichloromethane (2.0 mL) was added a saturated solution of HCl in diethyl ether (15 mL). The reaction mixture was stirred for 4 hours. The product was collected by filtration and dried in vacuo to afford the title compound (58.0 mg, 70% yield). 1H NMR (400 MHz, CD3OD): δ 8.06 (d, 1H), 7.43 (s, 1H), 7.33 (m, 2H), 7.26 (m, 1H), 6.38 (d, 1H), 5.88 (s, 1H), 4.80 (m, 1H), 3.54-3.43 (m, 4H), 3.22 (m, 4H), 1.62 (d, 3H); MS (ESI) m/z: Calculated for C18H22ClN4O2: 360.14; Observed: 361.5 (M++1) [corresponding to the free base].

Workup

  1. filtrationThe product was collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-f114234677ef4493bf697edbb1faa7f5
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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