Triethylamine → HCID 66878476, compound

HRID 880494Notes

Reaction equation

HRID 880494 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[N:18]=3)[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.C(N(CC)CC)C>C(OCC)(=O)C.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[N:18]=3)[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 668513301-(3-Chloro-4-nitro-phenyl)-4-(4,6-dimethyl-pyridin-2-yl)-piperazine

Product 1

HCID 66878476HCID 66878476, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Stannous chloride dihydrate (2.6 g, 11.5 mmol) was added to a solution of 1-(3-chloro-4-nitro-phenyl)-4-(4,6-dimethyl-pyridin-2-yl)-piperazine (800 mg, 2.31 mmol) in a mixture of ethyl acetate (20 mL) and ethanol (5 mL). The reaction mixture was heated at reflux for 2 h, allowed to cool to ambient temperature and basified with triethylamine. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography over neutral alumina with 10% ethyl acetate in petroleum ether as eluent to afford 2-chloro-4-[4-(4,6-dimethyl-2-pyridyl)piperazin-1-yl]aniline (470 mg, 64%) as a viscous light brown oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. customThe residue was purified by column chromatography over neutral alumina with 10% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-c9dd6751cfb64cb5bbd0df92fd379eaa
Source dataset
uspto-grants-2015_03
Patent number
US08993574B2

Reaction notes

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