Sodium Hydroxide → N1,N1'-([1,1'-Biphenyl]-3,5-diylbis(methylene))bis(N3-(3-(isobutylamino)propyl)propane-1,3-diamine)

HRID 58989Notes

Reaction equation

HRID 58989 reaction equation
[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[C:5]([CH:7]=O)[CH:4]=[C:3]([CH:9]=O)[CH:2]=1.NCCC[N:21]([CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:22][CH2:23][CH2:24][NH2:25].[BH4-].[Na+].[OH-].[Na+]>CO>[C:1]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[C:5]([CH2:7][NH:21][CH2:26][CH2:27][CH2:28][NH:25][CH2:24][CH2:23][CH2:22][NH:21][CH2:26][CH:27]([CH3:29])[CH3:28])[CH:4]=[C:3]([CH2:9][NH:25][CH2:24][CH2:23][CH2:22][NH:25][CH2:24][CH2:23][CH2:22][NH:21][CH2:26][CH:27]([CH3:28])[CH3:29])[CH:2]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 14199327[1,1'-Biphenyl]-3,5-dicarboxaldehydeHCID 57163134N'-(3-aminopropyl)-N3-isobutylpropane-1,3-diamine

Product 1

HCID 117718407N1,N1'-([1,1'-Biphenyl]-3,5-diylbis(methylene))bis(N3-(3-(isobutylamino)propyl)propane-1,3-diamine)

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[1,1′-Biphenyl]-3,5-dicarbaldehyde (3.03 g, 14.4 mmol) and MeOH (60 mL) were added to a round-bottom flask. To the solution was added N′-(3-aminopropyl)-N3-isobutylpropane-1,3-diamine (5.40 g, 28.8 mmol), and the reaction mixture was stirred at rt for 24 h. Sodium borohydride (0.55 g, 14.4 mmol) was added, and the reaction mixture was stirred for 2 h. The reaction mixture was concentrated under reduced pressure to afford a white solid. Aqueous NaOH (10%, 50 mL) was added, and the reaction mixture stirred for 30 min. The solution was extracted with CHCl3 (3×75 mL). The organic layers were combined, dried over Na2SO4, filtered, and concentrated under reduced pressure to afford a clear oil which was used without further purification.

Workup

  1. stirringthe reaction mixture was stirred for 2 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto afford a white solid
  4. stirringthe reaction mixture stirred for 30 min
  5. extractionThe solution was extracted with CHCl3 (3×75 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto afford a clear oil which
  10. customwas used without further purification

Sources & evidence

ORD record
ord-e532278bb88941b483d41e7527ca7f02
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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