1-Methylpiperazine → HCID 86720948, compound

HRID 524892Notes

Reaction equation

HRID 524892 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Cl:8][C:9]1[CH:14]=[C:13](Cl)[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][N:10]=1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:8][C:9]1[CH:14]=[C:13]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[C:12]([N+:16]([O-:18])=[O:17])=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 122757652,4-Dichloro-5-nitropyridine

Product 1

HCID 86720948HCID 86720948, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-methylpiperazine (298.5 mg, 330.6 μL, 2.980 mmol) in THF (5 mL) was added to a stirred solution of 2,4-dichloro-5-nitro-pyridine (500 mg, 2.591 mmol) and DIPEA (401.8 mg, 541.5 μL, 3.109 mmol) in THF (10 mL) at 0° C. under an atmosphere of nitrogen. The reaction was allowed to stir at ambient temperature for 1 hour then the solvent removed in vacuo. The residue was purified by column chromatography (ISCO Companion, 40 g column, eluting with 0 to 10% MeOH/DCM solutions) to give 1-(2-chloro-5-nitropyridin-4-yl)-4-methylpiperazine as a yellow solid (638 mg, 96% Yield). MS (ES+) 257.1.

Workup

  1. customthe solvent removed in vacuo
  2. customThe residue was purified by column chromatography (ISCO Companion, 40 g column, eluting with 0 to 10% MeOH/DCM solutions)

Sources & evidence

ORD record
ord-1fa7e151c7204b86acbc5d58367c5c26
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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