Hydrazine hydrate (1:1) → (2S)-2-(4-Fluorophenyl)propan-1-amine
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([CH3:21])[CH2:9][N:10]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:4][CH:3]=1.O.NN>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([CH3:21])[CH2:9][NH2:10])=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a room-temperature solution of (S)-2-(2-(4-fluorophenyl)propyl)isoindoline-1,3-dione (900 mg, 3.2 mmol, 1.0 equiv) in toluene (14 mL) was added hydrazine hydrate (1.4 mL, 45 mmol, 14 equiv) by syringe. The resulting mixture was heated to 80° C. for 30 minutes and then cooled to room temperature. The resulting solution was decanted from the solid in the reaction mixture, and the solid was washed with additional toluene. The combined organic layers were combined and concentrated in vacuo to provide the title compound (491 mg, 99%), which was used without further purification.
Workup
- temperaturecooled to room temperature
- customThe resulting solution was decanted from the solid in the reaction mixture
- washthe solid was washed with additional toluene
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-8d1d48f186c94494a113932aaae4c32f
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018223B2
Reaction notes
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