N,N-Dimethyl-1,3-propanediamine → HCID 68793200, compound

HRID 1161017Notes

Reaction equation

HRID 1161017 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:11]([CH3:24])([CH3:23])[C:12]([N:14]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:25][N:26]([CH3:31])[CH2:27][CH2:28][CH2:29][NH2:30].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.O>[CH3:25][N:26]([CH3:31])[CH2:27][CH2:28][CH2:29][NH:30][C:2]1[CH:3]=[C:4]([C:11]([CH3:24])([CH3:23])[C:12]([N:14]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

7

Reactant 3

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 11430Potassium CarbonateHCID 68448515HCID 68448515, compound

Product 1

HCID 68793200HCID 68793200, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(3-chloro-4-nitrophenyl)-N,N-diisobutyl-2-methylpropanamide (78 mg, 1 eq), 3-dimethylaminopropylamine (45 mg, 2 eq) and potassium carbonate (62 mg, 2 eq) in DMF (2 ml) is heated under reflux for 3 hours then cooled down to ambient temperature. The residue is taken up in ethyl acetate (20 ml) and water (8 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: 100% dichloromethane to dichloromethane/methanol 8:2) produces the expected compound in the form of a yellow oil (44 mg; 48% yield).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 3 hours
  3. extractionAfter decantation and extractions
  4. washthe combined organic phases are washed with salt water
  5. dry with materialdried over Na2SO4
  6. concentrationthen concentrated under reduced pressure at 40° C
  7. customPurification of the residue by flash chromatography on silica gel (eluent: 100% dichloromethane to dichloromethane/methanol 8:2)

Sources & evidence

ORD record
ord-b45bf95dda6c49e4ba59891ac134fe2d
Source dataset
uspto-grants-2010_10
Patent number
US07816539B2

Reaction notes

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