Benzylamine → 1-Benzyl-4-(propan-2-yl)-1,4-azaphosphinane 4-oxide
Reaction equation
[CH:1]([P:3](=[O:9])([CH:7]=[CH2:8])[CH:4]([CH3:6])[CH3:5])=[CH2:2].[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O>[CH2:10]([N:17]1[CH2:8][CH2:7][P:3](=[O:9])([CH:4]([CH3:6])[CH3:5])[CH2:1][CH2:2]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
A 20 L four-necked round bottom flask fitted with an overhead stirrer and reflux condenser, flame dried and cooled in a stream of nitrogen, was charged with the product of Step 1 (250 g, 1734 mmol), THE (2500 mL), water (2500 mL) and benzyl amine (297.3 g, 2774 mmol). The reaction mixture was heated at 85° C. for 16 h. After completion, THF was removed under reduced pressure. The aqueous layer was extracted with ether to remove the excess of benzyl amine and later with dichloromethane (2×2500 mL). The combined dichloromethane layers were washed with brine (2×1000 mL), dried over sodium sulfate and concentrated to give 1-benzyl-4-(propan-2-yl)-1,4-azaphosphinane 4-oxide (273 g, 63%) as brown oil.
Workup
- customA 20 L four-necked round bottom flask fitted with an overhead stirrer
- temperaturereflux condenser
- temperatureflame
- customdried
- temperaturecooled in a stream of nitrogen
- customAfter completion, THF was removed under reduced pressure
- extractionThe aqueous layer was extracted with ether
- customto remove the excess of benzyl amine
- washThe combined dichloromethane layers were washed with brine (2×1000 mL)
- dry with materialdried over sodium sulfate
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6e6a6f8066e240b98b23069bdd4bbc05
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08759366B2
Reaction notes
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