Diisopropylamine → N,N'-Diethyl-N-phenylhydrazine
Reaction equation
Cl.Cl.[CH2:3]([NH:5][NH:6][CH2:7][CH3:8])[CH3:4].Br[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC([O-])(C)C.[Na+].C(NC(C)C)(C)C>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:3]([N:5]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[NH:6][CH2:7][CH3:8])[CH3:4]Participants
7
Conditions
- Temperature
- 80 °C
Procedure
1,2-Diethylhydrazine dihydrochloride (1.2 equiv., 0.6 mmol, 97 mg), bromobenzene (1.0 equiv., 0.5 mmol, 0.05 mL), Pd(OAc)2 (0.05 equiv, 0.025 mmol, 6 mg), BINAP (0.05 equiv., 0.025 mmol, 16 mg), and NaOtBu (3.8 equiv., 1.9 mmol, 183 mg) and diisopropylamine (2 mL) were added to a flame dried test tube which was capped with a septum and purged briefly with argon (˜1 min.) and then heated to 80° C. for 4 hours. The reaction was then cooled to room temperature, diluted with Et2O (2 mL), filtered through Celite and concentrated under vacuum. The crude mixture was purified by flash column chromatography (2% EtOAc/Hex) to give the title product as a viscous yellow oil (27 mg, 0.16 mmol, 33% yield).
Workup
- customdried test tube which
- customwas capped with a septum
- custompurged briefly with argon (˜1 min.)
- temperatureThe reaction was then cooled to room temperature
- additiondiluted with Et2O (2 mL)
- filtrationfiltered through Celite
- concentrationconcentrated under vacuum
- customThe crude mixture was purified by flash column chromatography (2% EtOAc/Hex)
Sources & evidence
- ORD record
- ord-fde8ca9ff3694dc78259681d11e537a8
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06235936B1
Reaction notes
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