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

HRID 2425979Notes

Reaction equation

HRID 2425979 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]([NH:13][C:14]2[CH:15]=[C:16]([N:23]3[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)[CH:17]=[CH:18][C:19]=2[N+:20]([O-:22])=[O:21])[CH3:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[ClH:36]>ClCCl.C(OCC)C>[ClH:36].[CH3:10][O:9][C:7]1[CH:6]=[C:5]([CH:11]([NH:13][C:14]2[CH:15]=[C:16]([N:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]3)[CH:17]=[CH:18][C:19]=2[N+:20]([O-:22])=[O:21])[CH3:12])[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58707341t-Butyl 4-(3-(1-(3,5-dimethoxyphenyl)ethylamino)-4-nitrophenyl)piperazine-1-carboxylate

Product 1

HCID 67147330N-(1-(3,5-Dimethoxyphenyl)ethyl)-2-nitro-5-(piperazin-1-yl)benzenamine hydrochlorideYield 76%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl 4-(3-(1-(3,5-dimethoxyphenyl)ethylamino)-4-nitrophenyl)piperazine-1-carboxylate (327 mg, 0.67 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 (216 mg, 76% yield). 1H NMR (400 MHz, CD3OD): δ 8.03 (d, 1H), 6.55 (s, 2H), 6.36 (m, 2H), 5.95 (s, 1H), 4.67 (m, 1H), 3.73 (s, 6H), 3.49 (m, 4H), 3.29 (m, 4H), 1.60 (d, 3H); MS (ESI) m/z: Calculated for C20H27N4O4: 387.2; Observed: 387.3 (M++1) [corresponding to the free base].

Workup

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

Sources & evidence

ORD record
ord-0e65f5716a9d499090145b0dadd34b7f
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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