Reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([C:13]2([C:18]#[N:19])[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[Na+].O>C1COCC1.CCOCC>[C:7]1([C:13]2([CH2:18][NH2:19])[CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a stirring (mechanical stirring) suspension of 12 gm (0.315 mol) of lithium aluminum hydride in THF (600 ml) in a 2000 ml reaction flask at 0° C. (ice-bath), 35 gm (0.20 mol) of phenylcyclopentane carbonitrile in 100 ml THF is added dropwise via an addition funnel. The ice bath is replaced with a heating mantle and the reaction is heated at reflux for 16 hours. The reaction mixture is diluted with 500 ml ether and cooled down to 0° C. The reaction is worked up by adding 50 ml of 15 wt. % NaOH aqueous solution dropwise with vigorous stirring. Then 20 ml water is added and the mixture is stirred for an addition 10 minutes. The resulting two-phase mixture (a colorless liquid and a white precipitate) is filtered and the filtrate dried over anhydrous MgSO4. Filtration and concentration at reduced pressure on a rotary evaporator gave 33 gm of [(phenylcyclopentyl)methyl]amine.
Workup
- additionis added dropwise via an addition funnel
- temperaturethe reaction is heated
- temperatureat reflux for 16 hours
- filtrationThe resulting two-phase mixture (a colorless liquid and a white precipitate) is filtered
- dry with materialthe filtrate dried over anhydrous MgSO4
- filtrationFiltration and concentration at reduced pressure
- customon a rotary evaporator
Sources & evidence
- ORD record
- ord-437cf955e03e4ce184babcc7789df2b3
- Source dataset
- uspto-grants-2003_10
- Patent number
- US06632417B2
Linked notes
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