Reaction equation
C([NH2:8])C1C=CC=CC=1.[O:9]1[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:10]1>>[NH2:8][CH2:10][CH:11]([OH:9])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]Participants
3
Conditions
- Temperature
- 100 °C
Procedure
A 500-ml flask equipped with a stirrer was charged with 160 g (1.5 mol) of benzylamine, to which 29 g (0.11 mol) of 1,2-epoxyoctadecane were added dropwise over 3 hours while stirring at 100° C. Stirring was conducted further for 12 hours at 100° C. Benzyl alcohol was distilled off under reduced pressure, and the residue was charged into a 500-ml autoclave, to which 300 ml of ethanol and 10 g of 5% Pd/C were added to conduct hydrogenolysis for 48 hours at room temperature under a hydrogen pressure of 5 atm. After the catalyst was separated by filtration, the filtrate was concentrated under reduced pressure, and the residue was recrystallized from hexane, thereby obtaining 26.1 g (yield: 83%) of the title compound (IIh-7).
Workup
- customA 500-ml flask equipped with a stirrer
- additionwere added dropwise over 3 hours
- stirringStirring
- distillationBenzyl alcohol was distilled off under reduced pressure
- additionthe residue was charged into a 500-ml autoclave, to which 300 ml of ethanol and 10 g of 5% Pd/C
- additionwere added
- customfor 48 hours
- customat room temperature
- customAfter the catalyst was separated by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- customthe residue was recrystallized from hexane
Sources & evidence
- ORD record
- ord-6f171f3959e24ce6acc5b2cc1ccb94f6
- Source dataset
- uspto-grants-1998_03
- Patent number
- US05723497
Linked notes
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