N,N-dimethyl-p-phenylenediamine → N4-Heptyl-N1,N1-dimethyl-1,4-benzenediamine

HRID 1457599Notes

Reaction equation

HRID 1457599 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C(=O)([O-])O.[Na+]>ClCCl.C(O)(=O)C>[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 7472N,N-dimethyl-p-phenylenediamineHCID 8130HeptanalHCID 516892Sodium BicarbonateHCID 2724942Triacetoxyborohydride

Product 1

HCID 22099398N4-Heptyl-N1,N1-dimethyl-1,4-benzenediamineYield 46.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.50 g of N,N-dimethyl-p-phenylenediamine, 4.592 g of heptanal, 9.095 g of triacetoxyborohydride, 1.841 g of acetic acid and 257 ml of dichloromethane was stirred at room temperature for one hour. A saturated sodium hydrogen carbonate solution is added to the mixture, and the mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure. The residue obtained was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=2:1) to give 2.819 g of N,N-dimethyl-N'-heptyl-p-phenylenediamine (yield: 39%, oily product, IR (film): 3375, 2927, 1519 cm-1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed
  3. customdried
  4. customthe solvent was removed under reduced pressure
  5. customThe residue obtained
  6. customwas purified by silica gel column chromatography (solvent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-a456221f39354a91800f7687886e9831
Source dataset
uspto-grants-1998_12
Patent number
US05849732

Reaction notes

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