N,N'-Bis(1-methylpropyl)-1,4-benzenediamine → HCID 58241693, compound

HRID 2367920Notes

Reaction equation

HRID 2367920 reaction equation
[CH:1]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][CH:13]([CH2:15][CH3:16])[CH3:14])=[CH:8][CH:7]=1)([CH2:3][CH3:4])[CH3:2].[Na].[CH2:18]([CH:20]([CH2:23][CH2:24][CH2:25][CH3:26])[CH:21]=O)[CH3:19]>ClCCl>[CH:13]([N:12]([CH2:21][CH:20]([CH2:18][CH3:19])[CH2:23][CH2:24][CH2:25][CH3:26])[C:9]1[CH:8]=[CH:7][C:6]([N:5]([CH:1]([CH2:3][CH3:4])[CH3:2])[CH2:21][CH:20]([CH2:18][CH3:19])[CH2:23][CH2:24][CH2:25][CH3:26])=[CH:11][CH:10]=1)([CH2:15][CH3:16])[CH3:14]

Participants

5

Reactant 3

HCID 7589N,N'-Bis(1-methylpropyl)-1,4-benzenediamineHCID 312412-EthylhexanalHCID 5360545Sodium

Product 1

HCID 58241693HCID 58241693, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N,N′-di-sec-butyl-p-phenylenediamine (20.8 g, 94 mmol) and sodium triacetoxyhydroborate (60.0 g, 283 mmol) in dichloromethane (500 ml) was treated with 2-ethylhexanal (30.3 g, 236 mmol) and stirred at room temperature for 15 hours. TLC showed the reaction complete and the reaction mixture was decanted to a beaker and quenched by addition of saturated aqueous NaHCO3 and stirred until effervescence ceased. The organic phase was separated and washed twice with water, once with brine and then dried (MgSO4), filtered and concentrated in vaccuo to afford a red oil. The product was chromatographed (eluent 5% ethyl acetate in heptane). Relevant fractions were collected and concentrated to afford a red oil (36.16 g, 82% yield).

Workup

  1. customwas decanted to a beaker
  2. customquenched by addition of saturated aqueous NaHCO3
  3. stirringstirred until effervescence
  4. customThe organic phase was separated
  5. washwashed twice with water, once with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vaccuo
  9. customto afford a red oil
  10. customThe product was chromatographed (eluent 5% ethyl acetate in heptane)
  11. customRelevant fractions were collected
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-81688a45be73431ca611ff035b077812
Source dataset
uspto-grants-2014_04
Patent number
US08703682B2

Reaction notes

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