N-(2-Octyl)-p-phenylenediamine → N-(3-isopropoxypropyl)-N'-(2-octyl)-p-phenylenediamine

HRID 1658448

Reaction equation

HRID 1658448 reaction equation
[CH3:1][CH:2]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH:17]([O:20][CH2:21][CH2:22][CH:23]=O)([CH3:19])[CH3:18].[H][H]>CO.[Pt]=S>[CH:17]([O:20][CH2:21][CH2:22][CH2:23][NH:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][CH:2]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH3:1])=[CH:11][CH:12]=1)([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 584493N-(2-Octyl)-p-phenylenediamineHCID 186248553-(Propan-2-yloxy)propanalHCID 178418361HCID 178418361, compound

Product 1

HCID 21529417N-(3-isopropoxypropyl)-N'-(2-octyl)-p-phenylenediamine

Reagents, catalysts & solvents 2

HCID 82861Platinum sulfide (PtS)CatalystHCID 887MethanolSolvent

Procedure

A mixture of 20 g. of N-(2-octyl)-p-phenylenediamine, 14 g. of 3-isopropoxypropionaldehyde and 0.3g. of 5% platinum sulfide on carbon catalyzt is shaken in a rocker bomb at 150°C under 600 psi hydrogen for 5 hours. After allowing the mixture to cool to room temperature, the contents of the bomb are dissolved in methanol and filtered through celite. The filtrate is evaporated in vacuo and the residue is taken up in ether and treated with an excess of dry hydrogen chloride gas. The resulant solid is collected by filtration and recrystallized from methanol-acetone to yield the product N-(3-isopropoxypropyl)-N'-(2-octyl)-p-phenylenediamine in dihydrochloride salt form (mp 200°-202°C).

Workup

  1. additionA mixture of 20 g
  2. filtrationfiltered through celite
  3. customThe filtrate is evaporated in vacuo
  4. additiontreated with an excess of dry hydrogen chloride gas
  5. filtrationThe resulant solid is collected by filtration
  6. customrecrystallized from methanol-acetone

Sources & evidence

ORD record
ord-e2a2ba1f29a447c89f78d5be3f4f919e
Source dataset
uspto-grants-1976_06
Patent number
US03963780

Linked notes

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