Butylamine → N6-butyl-3-nitro-N2-(3-piperidin-1-ylpropyl)pyridine-2,6-diamine

HRID 1727040Notes

Reaction equation

HRID 1727040 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH2:11])[CH2:8][CH2:9][CH3:10].Cl[C:13]1[N:18]=[C:17]([NH:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)[C:16]([N+:29]([O-:31])=[O:30])=[CH:15][CH:14]=1>C(#N)C>[CH2:7]([NH:11][C:13]1[N:18]=[C:17]([NH:19][CH2:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[C:16]([N+:29]([O-:31])=[O:30])=[CH:15][CH:14]=1)[CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 8007ButylamineHCID 11430Potassium CarbonateHCID 860008436-chloro-3-nitro-N-(3-piperidin-1-ylpropyl)pyridin-2-amine

Product 1

HCID 86606889N6-butyl-3-nitro-N2-(3-piperidin-1-ylpropyl)pyridine-2,6-diamineYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

Potassium carbonate (930 mg, 2 eq) and a solution of 1-butylamine (300 mg, 1.2 eq) in acetonitrile (2 ml) are added successively to a solution of 6-chloro-3-nitro-N-(3-piperidin-1-ylpropyl)pyridin-2-amine (1 g, 1 eq; prepared according to Example A2) in acetonitrile (80 ml). The mixture is heated to reflux for 15 hours then cooled down to ambient temperature and concentrated under reduced pressure at 40° C. The residue is taken up in dichloromethane (200 ml) and water (90 ml). After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification of the residue obtained, by flash chromatography on silica gel (eluent: heptane/ethyl acetate 9:1 to 100% ethyl acetate), produces the expected compound (1.1 g; 98% yield).

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 15 hours
  3. concentrationconcentrated under reduced pressure at 40° C
  4. extractionAfter decantation and extractions
  5. washthe combined organic phases are washed with salt water
  6. dry with materialdried over Na2SO4
  7. concentrationthen concentrated under reduced pressure at 40° C
  8. customPurification of the residue
  9. customobtained, by flash chromatography on silica gel (eluent: heptane/ethyl acetate 9:1 to 100% ethyl acetate)

Sources & evidence

ORD record
ord-3aaa516cbcf74700a3da2049d4b1ebbf
Source dataset
uspto-grants-2009_02
Patent number
US07495009B2

Reaction notes

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