1-Phenethylpiperazine → HCID 57897205, compound

HRID 416938Notes

Reaction equation

HRID 416938 reaction equation
[CH2:1]([N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.Cl[C:25]1[C:30]([Cl:31])=[CH:29][N:28]=[C:27]([NH2:32])[C:26]=1[N+:33]([O-:35])=[O:34]>CC(O)C>[Cl:31][C:30]1[C:25]([N:12]2[CH2:11][CH2:10][N:9]([CH2:1][CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:14][CH2:13]2)=[C:26]([N+:33]([O-:35])=[O:34])[C:27]([NH2:32])=[N:28][CH:29]=1

Participants

5

Reactant 3

HCID 792141-PhenethylpiperazineHCID 81531DiisopropylethylamineHCID 468676602-Amino-4,5-dichloro-3-nitropyridine

Product 1

HCID 57897205HCID 57897205, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
65 °C

Procedure

1-Phenethylpiperazine (0.100 g, 0.52 mmol, 1.1 eq) was suspended in iPrOH (1 mL). DIPEA (0.13 mL, 0.79 mmol, 1.5 eq) was added followed by 4,5-dichloro-3-nitropyridin-2-amine (0.099 g, 0.48 mmol, 1 eq). The mixture was heated and stirred at 65° C. overnight. The mixture was cooled to room temperature and filtered. The bright yellow solid was washed with iPrOH (3×2 mL), Et2O (2×2 mL) and dried to give the title compound as a bright yellow solid (0.112 g, 64%); 1H-NMR (500 MHz, DMSO-d6): δ 2.53-2.63 (m, 6H), 2.71-2.78 (m, 2H), 3.06 (m, 4H, piperazine N(CH2)2), 6.95 (s, 2H, NH2), 7.15-7.21 (m, 1H), 7.22-7.31 (m, 4H), 8.06 (s, 1H, pyridine 6-H); LC (Method B)-MS (ESI, m/z): Rt=2.31 min—362/364 [(M+H)+, Cl isotopic pattern].

Workup

  1. temperatureThe mixture was heated
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. washThe bright yellow solid was washed with iPrOH (3×2 mL), Et2O (2×2 mL)
  5. customdried

Sources & evidence

ORD record
ord-b4fa144fcb84407d91c895547cbdcaca
Source dataset
uspto-grants-2012_01
Patent number
US08088761B2

Reaction notes

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