Dimethylformamide → HCID 86720925, compound

HRID 524866Notes

Reaction equation

HRID 524866 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].[CH3:17]N(C=O)C.[H-].[Na+].CI>>[CH3:1][CH:2]1[CH2:7][N:6]([CH3:17])[CH2:5][CH2:4][N:3]1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 62672841HCID 62672841, compound

Product 1

HCID 86720925HCID 86720925, compound

Procedure

To 2-methyl-1-(3-nitro-4-pyridyl)piperazine in DMF (1.5 mL of 0.3 M, 0.4500 mmol) at 0° C. was added NaH (18.00 mg, 0.4500 mmol). The reaction was stirred for 10 mins then MeI (60.68 mg, 26.61 μL, 0.4275 mmol) was added. The reaction mixture was stirred for 4 hours at RT and quenched by the addition of water. The crude was loaded onto a MeOH pre-washed SCX column, rinsed with MeOH and the product was released with methanolic ammonia. The ammonia extracts were concentrated under reduced pressure. The residue was purified by column chromatography eluting with 1-15% MeOH:DCM to yield 2,4-dimethyl-1-(3-nitropyridin-4-yl)piperazine. MS (ES+) 237.2.

Workup

  1. stirringThe reaction mixture was stirred for 4 hours at RT
  2. customquenched by the addition of water
  3. washrinsed with MeOH
  4. concentrationThe ammonia extracts were concentrated under reduced pressure
  5. customThe residue was purified by column chromatography
  6. washeluting with 1-15% MeOH

Sources & evidence

ORD record
ord-8c5ec105ad2541949aced50f3e677d5c
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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