Pyridine → 2-(4-Fluorophenyl)-1-phenylethan-1-amine
Reaction equation
CO[N:3]=[C:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1.B.C1COCC1.N1C=CC=CC=1.CCOC(C)=O>C1COCC1>[NH2:3][CH:4]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 2-(4-fluorophenyl)-1-phenyl-1-ethanone-O-methyl oxime (1.34 g, 4.62 mmol) in 30 ml dry THF under nitrogen was added borane-THF complex (1.0M in THF, 23.1 ml, 23.1 mmol) and dry pyridine (10 ml) by syringe at 25° C. The resulting bi-phasic solution was refluxed with vigorous magnetic stirring for 16 hours. After the reaction was cooled to 25° C. and was quenched with 10% NaOH solution, hexanes (50 ml) were added and the layers were separated. The aqueous portion was extracted with hexanes again (40 ml). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to yield a cloudy colorless syrup (3.55 g, 66% yield for two steps). Rf : 0.24 (EtOAc).
Workup
- temperatureThe resulting bi-phasic solution was refluxed with vigorous
- customwas quenched with 10% NaOH solution, hexanes (50 ml)
- additionwere added
- customthe layers were separated
- extractionThe aqueous portion was extracted with hexanes again (40 ml)
- dry with materialThe combined organic layers were dried over magnesium sulfate
- concentrationconcentrated in vacuo
- customto yield a cloudy colorless syrup (3.55 g, 66% yield for two steps)
Sources & evidence
- ORD record
- ord-d9f4d4017545483bba7f565631882877
- Source dataset
- uspto-grants-1997_11
- Patent number
- US05688789
Reaction notes
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