Benzyl 2-[({[2-(diisopropylamino)ethyl]amino}carbonyl)amino]ethylcarbamate → N-(2-aminoethyl)-N'-[2-(diisopropylamino)ethyl]urea

HRID 10463Notes

Reaction equation

HRID 10463 reaction equation
[CH:1]([N:4]([CH:24]([CH3:26])[CH3:25])[CH2:5][CH2:6][NH:7][C:8]([NH:10][CH2:11][CH2:12][NH:13]C(=O)OCC1C=CC=CC=1)=[O:9])([CH3:3])[CH3:2]>C(O)C.[OH-].[Pd+2].[OH-]>[NH3:4].[NH2:13][CH2:12][CH2:11][NH:10][C:8]([NH:7][CH2:6][CH2:5][N:4]([CH:24]([CH3:26])[CH3:25])[CH:1]([CH3:2])[CH3:3])=[O:9]

Participants

5

Reactant 1

HCID 21978301Benzyl 2-[({[2-(diisopropylamino)ethyl]amino}carbonyl)amino]ethylcarbamate

Product 2

HCID 222AmmoniaHCID 21978253N-(2-aminoethyl)-N'-[2-(diisopropylamino)ethyl]ureaYield 216.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of benzyl 2-[({[2-(diisopropylamino)ethyl]amino}carbonyl)amino]ethylcarbamate (Preparation 50) (6.25 g, 14.45 mmol) in ethanol (100 ml) was hydrogenated at room temperature over palladium (II) hydroxide (250 mg) for 4 hours at 414 KPa. The catalyst was removed by filtration through Arbocel (trade mark) and solvent evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol:concentrated aqueous ammonia (90:10:1, by volume) changing to dichloromethane:methanol:concentrated aqueous ammonia (90:10:2, by volume) to afford the title compound as a yellow oil (3.6 g).

Workup

  1. customThe catalyst was removed by filtration through Arbocel (trade mark) and solvent
  2. customevaporated under reduced pressure
  3. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane

Sources & evidence

ORD record
ord-4a6dcdf464c440f5b2372f95897642bd
Source dataset
uspto-grants-2006_08
Patent number
US07094769B2

Reaction notes

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