1-Methylpiperazine → HCID 58638509, compound

HRID 646927Notes

Reaction equation

HRID 646927 reaction equation
Cl[C:2]1[CH:3]=[C:4]([N:11]2[CH2:16][CH2:15][CH:14]([CH3:17])[CH2:13][CH2:12]2)[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>CN(C=O)C>[CH3:17][CH:14]1[CH2:15][CH2:16][N:11]([C:4]2[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=[C:2]([N:22]3[CH2:23][CH2:24][N:19]([CH3:18])[CH2:20][CH2:21]3)[CH:3]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 58638517HCID 58638517, compound

Product 1

HCID 58638509HCID 58638509, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 5′-chloro-4-methyl-2′-nitro-3,4,5,6-tetrahydro-2H-[1,3′]bipyridinyl (as prepared in the previous step) (255 mg, 1.00 mmol) in DMF (10 mL) was added 1-methyl piperazine (110 μL, 1.00 mmol). The resulting mixture was heated at 125° C. overnight. The reaction mixture was allowed to cool to room temperature and partitioned between water and EtOAc. The EtOAc layer was separated, dried (Na2SO4) and concentrated in vacuo. The residue obtained was purified on silica (10-50% EtOAc:hexane) to obtain the title compound (204 mg, 64%). 1H-NMR (CDCl3; 400 MHz): δ 7.67 (d, 1H, J=2.52 Hz), 6.69 (d, 1H, J=2.52 Hz), 3.39 (m, 4H), 3.29 (m, 2H), 2.75 (m, 2H), 2.56 (m, 4H), 2.35 (s, 3H), 1.71 (m, 2H), 1.6-1.5 (m, 3H), 0.99 (d, 3H, J=6.3 Hz).

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned between water and EtOAc
  3. customThe EtOAc layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue obtained
  7. customwas purified on silica (10-50% EtOAc:hexane)

Sources & evidence

ORD record
ord-5481daf1591640beb229a6e943ab076f
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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