Hydrochloric Acid → HCID 67147351, compound

HRID 1910527Notes

Reaction equation

HRID 1910527 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:8]=1.Cl>ClCCl.C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([N:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11617178HCID 11617178, compound

Product 1

HCID 67147351HCID 67147351, compoundYield 165.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3-chlorobenzyl)-4-nitro-3-(piperazin-1-yl)benzenamine (77 mg, 0.17 mmol) in dry dichloromethane (1.0 mL) was added a saturated solution of HCl in diethyl ether (15 mL). The reaction mixture was stirred for 4 hours. The solvent was evaporated and the precipitate was recrystallized from methanol (0.3 mL), dichloromethane (0.5 mL) and diethyl ether (5 mL). The product was collected by filtration and dried in vacuo to afford the title compound (54 mg, 82% yield after recrystallization). 1H NMR (400 MHz, CD3OD): δ 8.01 (d, 1H), 7.37-7.27 (m, 4H), 6.39 (d, 1H), 6.25 (s, 1H), 4.45 (s, 2H), 3.36 (m, 4H), 3.23 (m, 4H); MS (ESI) m/z: Calculated for C17H20ClN4O2: 347.13; Observed: 347.4 (M++1) [corresponding to the free base].

Workup

  1. customThe solvent was evaporated
  2. customthe precipitate was recrystallized from methanol (0.3 mL), dichloromethane (0.5 mL) and diethyl ether (5 mL)
  3. filtrationThe product was collected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-6f64de3c97da4bd3a2e3ca79f63899b5
Source dataset
uspto-grants-2013_12
Patent number
US08604021B2

Reaction notes

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