Ethylenediamine → 6-Cyano-2-octyl-indanone
Reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:8]2=[O:11])=[CH:4][CH:3]=1.[C:20]([Cu])#[N:21].CN(C)C=O.C(N)CN>O>[C:20]([C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH:7]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:8]2=[O:11])=[CH:4][CH:3]=1)#[N:21]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 160 °C
Procedure
Subsequently, 150 g (4.7×10-1M) of 6-bromo-2-octyl-1-indanone, 62.3 g (7.0×10-1M) of CuCN and 800 ml of dimethylformamide (DMF) were placed in a 2 liter-reaction vessel, followed by stirring for 6 hours at 160° C. After the reaction, the reaction mixture was cooled and poured into 3 liter of water and 100 ml of ethylenediamine was added, followed by extraction with ethyl acetate. The organic layer was washed with water, followed by drying with anhydrous magnesium sulfate and distilling-off of the solvent to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent: n-hexane/chloroform=1/1) to obtain 69.6 g of 6-cyano-2-octyl-1-indanone (Yield: 55%).
Workup
- customAfter the reaction
- temperaturethe reaction mixture was cooled
- additionwas added
- extractionfollowed by extraction with ethyl acetate
- washThe organic layer was washed with water
- dry with materialby drying with anhydrous magnesium sulfate and distilling-off of the solvent
- customto obtain a crude product
- customThe crude product was purified by silica gel column chromatography (eluent: n-hexane/chloroform=1/1)
Sources & evidence
- ORD record
- ord-32260335b70f400a84835d84d56da0fa
- Source dataset
- uspto-grants-1994_10
- Patent number
- US05354501
Reaction notes
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