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

HRID 58986Notes

Reaction equation

HRID 58986 reaction equation
[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[C:5]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH2:15][NH2:16])[CH:4]=[C:3]([CH2:17][NH:18][CH2:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][CH2:25][NH2:26])[CH:2]=1.[CH:33](=O)[CH:34]([CH3:36])[CH3:35].[BH4-].[Na+].[OH-].[Na+]>CCOC(C)=O.CO>[C:1]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:6]=[C:5]([CH2:7][NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][CH2:14][CH2:15][NH:16][CH2:33][CH:34]([CH3:36])[CH3:35])[CH:4]=[C:3]([CH2:17][NH:18][CH2:19][CH2:20][CH2:21][NH:22][CH2:23][CH2:24][CH2:25][NH:26][CH2:2][CH:1]([CH3:27])[CH3:6])[CH:2]=1

Participants

7

Reactant 4

HCID 6561IsobutyraldehydeHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 86273969N1,N1'-([1,1'-biphenyl]-3,5-diylbis(methylene))bis(N3-(3-aminopropyl)propane-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 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round-bottom flask was added the crude N1,N1′-([1,1′-biphenyl]-3,5-diylbis(methylene))bis(N3-(3-aminopropyl)propane-1,3-diamine) (3.5 g, 8.0 mmol) and MeOH (50 mL). To the solution was added isobutyraldehyde (1.15 g, 15.9 mmol) and the reaction mixture was stirred at rt for 24 h. Sodium borohydride (1.2 g, 31.9 mmol) was added and the reaction mixture was stirred for 1 h. The reaction mixture was concentrated under reduced pressure to afford a white solid. Aq. NaOH (10%, 200 mL) and EtOAc (200 mL) were added, and the mixture was stirred for 1 h. The layers were separated and the aqueous layer was extracted with EtOAc (200 mL). The combined organics were dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the desired product as a clear oil which was used without further purification.

Workup

  1. stirringthe reaction mixture was stirred for 1 h
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto afford a white solid
  4. stirringthe mixture was stirred for 1 h
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with EtOAc (200 mL)
  7. dry with materialThe combined organics were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f123b7b006064c7d80ffd2ceaf02ae05
Source dataset
uspto-grants-2016_09
Patent number
US09439433B2

Reaction notes

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