Ethylamine → 4-[3-(Ethylamino)-2-hydroxypropoxy]-benzonitrile
Reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[CH2:14]([NH2:16])[CH3:15]>C(#N)C>[CH2:14]([NH:16][CH2:3][CH:2]([OH:1])[CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)[CH3:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
86.0 g of 4-(oxiranylmethoxy) benzonitrile was dissolved in 250 ml acetonitrile and mixed with 29.7 g ethylamine in an autoclave. The mixture was heated in a boiling water-bath over night, evaporated and the residue was dissolved in 2-M hydrochloric acid. This acidic waterlayer was washed twice with ether, alkalized with 10-M sodium hydroxide and extracted with three portions of dichloromethane.
Workup
- temperatureThe mixture was heated in a boiling water-bath over night
- customevaporated
- dissolutionthe residue was dissolved in 2-M hydrochloric acid
- washThis acidic waterlayer was washed twice with ether
- extractionextracted with three portions of dichloromethane
Sources & evidence
- ORD record
- ord-4a26f771acd94d58a2cf9af214d0f416
- Source dataset
- uspto-grants-1992_10
- Patent number
- US05155133
Reaction notes
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