Hexane → alpha-(Cyclohexyl)-alpha,alpha-bis[2-(diisopropylamino)ethyl]acetamide
Reaction equation
[CH:1]([N:4]([CH:26]([CH3:28])[CH3:27])[CH2:5][CH2:6][C:7]([CH2:17][CH2:18][N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:8]([NH2:10])=[O:9])([CH3:3])[CH3:2].[H][H].CCCCCC>C(O)C.C(Cl)Cl.[Ru](=O)=O>[CH:11]1([C:7]([CH2:6][CH2:5][N:4]([CH:1]([CH3:3])[CH3:2])[CH:26]([CH3:28])[CH3:27])([CH2:17][CH2:18][N:19]([CH:20]([CH3:22])[CH3:21])[CH:23]([CH3:24])[CH3:25])[C:8]([NH2:10])=[O:9])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 125 °C
Procedure
10 Parts of α,α-bis[2-(diisopropylamino)ethyl]-α-phenylacetamide is dissolved in 130 parts by volume of ethanol and the solution placed in pressure shaker with 1 part of ruthenium dioxide. Hydrogen is introduced at 1000 psi and the reaction mixture heated at about 125° C. and shaken for about 24 hours. Then, the reaction mixture is cooled to room temperature and filtered. The filtrate is stripped of solvent to give an oil. This oil is dissolved in methylene chloride, then hexane added to the solution, methylene chloride evaporated, and the hexane mixture cooled to give α-(cyclohexyl)-α,α-bis[2-(diisopropylamino)ethyl]acetamide, as a crystal solid melting at about 114°-115° C. This compound has the following structural formula ##STR49##
Workup
- temperatureThen, the reaction mixture is cooled to room temperature
- filtrationfiltered
- customto give an oil
- customevaporated
- temperaturethe hexane mixture cooled
Sources & evidence
- ORD record
- ord-123a16f7f1c3485f89dc95d12ea3e4ae
- Source dataset
- uspto-grants-1980_08
- Patent number
- US04217306
Reaction notes
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