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

HRID 58981Notes

Reaction equation

HRID 58981 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.[NH2:17][CH2:18][CH2:19][CH2:20][NH:21][CH2:22][CH2:23][CH2:24][NH:25][CH2:26][CH2:27][CH2:28][CH3:29].[BH4-].[Na+].[OH-].[Na+]>CCOC(C)=O.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:17][CH2:18][CH2:19][CH2:20][NH:21][CH2:22][CH2:23][CH2:24][NH:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:4]=[C:3]([CH2:9][NH:17][CH2:18][CH2:19][CH2:20][NH:21][CH2:22][CH2:23][CH2:24][NH:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:2]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 12900282N1-(3-aminopropyl)-N3-butylpropane-1,3-diamineHCID 14199327[1,1'-Biphenyl]-3,5-dicarboxaldehyde

Product 1

HCID 117718406N1,N1'-([1,1'-biphenyl]-3,5-diylbis(methylene))bis(N3-(3-(butylamino)propyl)propane-1,3-diamine)

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

[1,1′-Biphenyl]-3,5-dicarbaldehyde (0.66 g, 3.15 mmol) and MeOH (50 mL) were added to a round-bottom flask. To the solution was added N1-(3-aminopropyl)-N3-butylpropane-1,3-diamine (1.18 g, 6.31 mmol) and the reaction mixture was stirred at rt for 24 h. Sodium borohydride (0.48 g, 12.62 mmol) was added and the reaction mixture stirred for 1 h. The reaction mixture was concentrated under reduced pressure to afford a white solid. Aq. NaOH (10%, 100 mL) and EtOAc (100 mL) were added and the reaction mixture stirred for 1 h. The layers were separated and the aqueous layer was extracted with EtOAc (100 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 stirred for 1 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto afford a white solid
  4. stirringthe reaction mixture stirred for 1 h
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with EtOAc (100 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customto afford a clear oil which
  11. customwas used without further purification

Sources & evidence

ORD record
ord-78bcbd6f54454407b30e951d70427a85
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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