1-Methylpiperazine → HCID 86720948, compound

HRID 524901Notes

Reaction equation

HRID 524901 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, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-methylpiperazine (119.3 mg, 132.6 μL, 1.191 mmol) in THF (1.5 mL) was added to a stirred solution of 2,4-dichloro-5-nitro-pyridine (200 mg, 1.036 mmol) and DIPEA (160.6 mg, 216.4 μL, 1.243 mmol) in THF (3.000 mL) at 0° C. under an atmosphere of nitrogen. The reaction was allowed to stir at ambient temperature overnight. The reaction mixture was partitioned between ethyl acetate and NaHCO3 (sat. aq. soln). The combined organics was washed with brine, dried over MgSO4 and concentrated under reduced pressure to yield 1-(2-chloro-5-nitro-4-pyridyl)-4-methyl-piperazine. (100%) MS (ES+) 257.1.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and NaHCO3 (sat. aq. soln)
  2. washThe combined organics was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-49b2f9b1d22148efab7fa52ffa40d521
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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