HCID 19698847, compound → HCID 14791327, compound

HRID 2256646Notes

Reaction equation

HRID 2256646 reaction equation
[NH2:1][CH:2]([CH3:33])[CH2:3][CH2:4][N:5](CC1C=CC=CC=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]([CH2:21][CH2:22][CH:23]([NH2:25])[CH3:24])CC1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].C(O)C>[NH2:25][CH:23]([CH3:24])[CH2:22][CH2:21][NH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3][CH:2]([NH2:1])[CH3:33]

Participants

5

Reactant 2

HCID 19698847HCID 19698847, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14791327HCID 14791327, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Combine N,N'-bis[3-(amino)butyl]-N,N'-bis[(phenyl)methyl]-1,7-diaminoheptane (13.4 g, 0.029 mol), Pearlman's Catalyst (2.0 g) and ethanol (90 ml) and treat the mixture with hydrogen gas at 45 lb/in2 until gas uptake ceases. Remove the catalyst by filtration and remove the solvent in vacuo to obtain 7.7 g of N,N'-bis[3-(amino)butyl]-1,7-diaminoheptane (Rf is 0.37 for TLC on silica gel developed with 40% conc. ammonia in methanol). Dissolve the residue in dichloromethane (90 ml) and treat the mixture with di-t-butyldicarbonate (26.2 g, 0.12 mol) for 3 hours. Remove the solvent in vacuo and purify the residue by flash chromatography on silica gel eluting with 25% ethyl acetate in hexane to yield 17.1 g of the title compound as a clear oil. Rf is 0.35 for TLC on silica gel developed with 25% ethyl acetate in hexane.

Workup

  1. customRemove the catalyst
  2. filtrationby filtration
  3. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-8e8d5357f9fe4ee486c2a0e6f5a1d2c3
Source dataset
uspto-grants-1997_08
Patent number
US05654484

Reaction notes

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