Water → 4-(Dimethylamino)-2-(naphthalen-1-yl)butanenitrile
Reaction equation
[NH2-].[Na+].[C:3]1([CH2:13][C:14]#[N:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.Cl[CH2:17][CH2:18][N:19]([CH3:21])[CH3:20].O>C1C=CC=CC=1>[CH3:20][N:19]([CH3:21])[CH2:18][CH2:17][CH:13]([C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1)[C:14]#[N:15]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
6.9 g of sodium amide are added in small portions to 29.4 g of naphth-1-ylacetonitrile in 250 ml of anhydrous benzene and the mixture is heated at 80° C. for 2 hours. It is cooled to +40° C., 19 g of 2-chlorodimethylaminoethane are added dropwise and the mixture is then heated again at 80° C. for 4 hours. It is cooled and 200 ml of water are added. After decantation, the organic phase is extracted with a 10% solution of hydrochloric acid. The aqueous phase is washed with ether, neutralized with a 10% solution of sodium hydroxide and extracted with ether and the extract is then washed with water and dried over sodium sulfate. 24 g of the expected product are obtained after evaporation of the solvent.
Workup
- temperatureIt is cooled to +40° C.
- temperaturethe mixture is then heated again at 80° C. for 4 hours
- temperatureIt is cooled
- extractionAfter decantation, the organic phase is extracted with a 10% solution of hydrochloric acid
- washThe aqueous phase is washed with ether
- extractionextracted with ether
- washthe extract is then washed with water
- dry with materialdried over sodium sulfate
Sources & evidence
- ORD record
- ord-71a25e76d44e4542a72282455eac04cc
- Source dataset
- uspto-grants-1990_04
- Patent number
- US04916156
Reaction notes
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