Potassium Carbonate → N,N-bis(3-methylbutyl)-4-nitro-3-[(3-piperidin-1-ylpropyl)amino]benzamide

HRID 899910Notes

Reaction equation

HRID 899910 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[C:5]([N:7]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6].[N:24]1([CH2:30][CH2:31][CH2:32][NH2:33])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:11][CH:10]([CH3:12])[CH2:9][CH2:8][N:7]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:5](=[O:6])[C:4]1[CH:18]=[CH:19][C:20]([N+:21]([O-:23])=[O:22])=[C:2]([NH:33][CH2:32][CH2:31][CH2:30][N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 19049Piperidine-1-propylamineHCID 684471113-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide

Product 1

HCID 68446148N,N-bis(3-methylbutyl)-4-nitro-3-[(3-piperidin-1-ylpropyl)amino]benzamideYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide (430 mg, 1 eq, prepared according to Example A1), 3-piperidino-propylamine (212 mg, 1.1 eq) and potassium carbonate (365 mg, 2 eq) in acetonitrile (10 ml) is heated under reflux for 3 hours then concentrated under reduced pressure at 40° C. The residue is taken up in dichloromethane (50 ml) and water (20 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 by flash chromatography on silica gel (eluent: ethyl acetate 100%) produces the expected compound in the form of a yellow oil (460 mg; 78% yield).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. concentrationthen concentrated 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 by flash chromatography on silica gel (eluent: ethyl acetate 100%)

Sources & evidence

ORD record
ord-7648f6e127604772a5e58a726f575ffd
Source dataset
uspto-grants-2008_04
Patent number
US07355052B2

Reaction notes

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