Butylamine → 1-Butyl-3-pyrroline
Reaction equation
[CH3:1]/[CH:2]=[CH:3]\[CH3:4].[CH2:5]([NH2:9])[CH2:6][CH2:7][CH3:8]>C1(C)C=CC=CC=1>[CH2:1]([N:9]1[CH2:8][CH:7]=[CH:6][CH2:5]1)[CH2:2][CH2:3][CH3:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
To a solution of 60.0 g of the cis-2-butene derivative solution prepared in Example 1 and 250 g of toluene in a round flask reactor, 117.0 g (1.6 mol) of butylamine was added dropwise with stirring for 30 min. at about 5° C. using an ice-bath. After 2 hours of stirring, the crystallized solid was removed by filtration; 42.0 g of 35% HCl (aq) was added to the filtrate, and then excess benzylamine hydrochloride was removed by filtration or extraction. After the solvent was evaporated under reduced pressure, 46.1 g of 1-butyl-3-pyrroline (yield 92.0%) was obtained.
Workup
- stirringAfter 2 hours of stirring
- customthe crystallized solid was removed by filtration
- addition42.0 g of 35% HCl (aq) was added to the filtrate
- customexcess benzylamine hydrochloride was removed by filtration or extraction
- customAfter the solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-d9494f9614bf471badf8607d19a70958
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06130338
Reaction notes
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