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

HRID 1658449Notes

Reaction equation

HRID 1658449 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1)([CH3:3])[CH3:2].[CH3:16][CH:17](Br)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].C(=O)([O-])[O-].[Na+].[Na+].C(O)C>O>[CH:1]([O:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][CH:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH3:16])=[CH:11][CH:10]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 79046Sec-octyl bromide, (+-)-HCID 21529410N-(3-isopropoxypropyl)-p-phenylenediamine

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 50 g. of N-(3-isopropoxypropyl)-p-phenylenediamine, 50 g. of 2-octyl bromide, 200 ml. of 2N sodium carbonate and 1 liter of ethanol is stirred for 18 hours at 60°C. The reaction mixture is treated with 1 liter of water and extracted with 1 liter of ether. The ether layer is separated, washed with 1200 ml. of water, dried over sodium sulfate and evaporated in vacuo. A mixture of the residue in ether is treated with hydrogen chloride gas to yield the title product in dihydrochloride salt form, m.p. 200°-202°C.

Workup

  1. additionA mixture of 50 g
  2. extractionextracted with 1 liter of ether
  3. customThe ether layer is separated
  4. washwashed with 1200 ml
  5. dry with materialof water, dried over sodium sulfate
  6. customevaporated in vacuo
  7. additionA mixture of the residue in ether
  8. additionis treated with hydrogen chloride gas

Sources & evidence

ORD record
ord-b7c96a907a3a4aa2af5df0a06d2a85f6
Source dataset
uspto-grants-1976_06
Patent number
US03963780

Reaction notes

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