Reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][C:4]([CH2:7][C:8]#[N:9])=[CH:3][CH:2]=1.Cl[CH2:17][CH2:18][N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21].[OH-].[Na+]>[Br-].C([N+](C)(C)C)C1C=CC=CC=1.C(Cl)Cl.O>[C:1]1([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:2]=[CH:3][C:4]([CH:7]([CH2:17][CH2:18][N:19]([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21])[C:8]#[N:9])=[CH:5][CH:6]=1Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
The mixture of 50 parts of α-(4-biphenylyl)acetonitrile, 45.8 parts of 2-chloro-N,N-diisopropylethylamine, 80 parts by volume of 50% sodium hydroxide, 250 parts by volume of methylene chloride and 1 part of benzyltrimethylammonium bromide is stirred at room temperature with slight cooling in an icy water bath for about 24 hours. The mixture is then poured into water and to this mixture additional quantity of methylene chloride is added. The organic layer is separated, washed with water, dried over anhydrous sodium sulfate and concentrated to afford α-(4-biphenylyl)-α-[2-(diisopropylamino)ethyl]acetonitrile, as a solid. This compound is identical to that of Example 1.
Workup
- temperaturewith slight cooling in an icy water bath for about 24 hours
- additionis added
- customThe organic layer is separated
- washwashed with water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bee095f34501411d9fb398a67f21a714
- Source dataset
- uspto-grants-1980_08
- Patent number
- US04217306
Linked notes
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