Sodium Hydroxide → (4-Nitrobenzyl)dipropylamine

HRID 1173850Notes

Reaction equation

HRID 1173850 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([O-:4])=[O:3].[OH-].[Na+]>C(Cl)(Cl)Cl>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]([CH2:7][CH2:8][CH3:9])[CH2:6][CH2:5][CH3:12])=[CH:11][CH:12]=1)([O-:4])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 112524674-Nitrobenzylamine hydrochloride

Product 1

HCID 15871689(4-Nitrobenzyl)dipropylamineYield 146.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Commercially available 4-nitrobenzylamine hydrochloride (manufactured by Tokyo Kasei Kogyo., Ltd.) (1.82 g) was suspended in chloroform (15 ml). Then, a 1 mol/l sodium hydroxide aqueous solution (15 ml) was added to the suspension and the aqueous layer was then extracted with chloroform. The extract was dried with anhydrous magnesium sulfate and the solvent was then distilled off, followed by dissolving the residue in anhydrous methanol (20 ml). Subsequently, the solution was added with propionaldehyde (1.66 ml) and sodium cyanoborohydride (1.81 g) and then adjusted to pH 5 with acetic acid, followed by stirring at room temperature for 21 hours. After completion of the reaction, the solvent was distilled off. The residue was added with 1 mol/l sodium hydroxide and then subjected to chloroform extraction. The extract was dried with anhydrous magnesium sulfate and the solvent was then distilled off. The residue was purified through silica gel column chromatography (hexane/ethyl acetate), thereby obtaining the subject compound (1.67 g) as a yellow oily substance.

Workup

  1. extractionthe aqueous layer was then extracted with chloroform
  2. dry with materialThe extract was dried with anhydrous magnesium sulfate
  3. distillationthe solvent was then distilled off
  4. dissolutionby dissolving the residue in anhydrous methanol (20 ml)
  5. additionSubsequently, the solution was added with propionaldehyde (1.66 ml) and sodium cyanoborohydride (1.81 g)
  6. customAfter completion of the reaction
  7. distillationthe solvent was distilled off
  8. additionThe residue was added with 1 mol/l sodium hydroxide
  9. extractionsubjected to chloroform extraction
  10. dry with materialThe extract was dried with anhydrous magnesium sulfate
  11. distillationthe solvent was then distilled off
  12. customThe residue was purified through silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cb9ba3db611d4dcd81a5b2f5cb884a92
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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