Diethyl Ether → (7-bromo-9H-fluoren-2-yl)-dibutyl amine
Reaction equation
[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8]C(N)=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1.IC[CH2:18][CH2:19][CH3:20].[C:21](=O)([O-])[O-].[K+].[K+].[CH3:27][N:28]([CH3:31])[CH:29]=O.C(O[CH2:35][CH3:36])C>O>[Br:1][C:2]1[CH:14]=[C:13]2[C:5]([C:6]3[CH:7]=[CH:8][C:27]([N:28]([CH2:31][CH2:21][CH2:35][CH3:36])[CH2:29][CH2:18][CH2:19][CH3:20])=[CH:10][C:11]=3[CH2:12]2)=[CH:4][CH:3]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 120 °C
Procedure
Under N2 atmosphere, 0.52 parts of 7-bromo-9H-fluoren-2-ylamine, 1.47 parts of 1-iodobutane, and 1.38 parts of potassium carbonate were added into 15 parts of dry dimethylformamide, followed by stirring and mixing. Then, the reaction mixture was heated to 120° C. and reacted for 24 hours. After the reaction mixture was cooled, poured the water into the reaction mixture for quenching the reaction, and using the diethyl ether to extract the product, and magnesium sulfate was used for dehydration. After removing the solvent, the residual was purified with column chromatography method by using dichloromethane/hexane co-solvent as an eluent, to obtain a compound (11) of the present example. This compound was in a form of a yellowish-brown solid, and the yield of this compound was 85%.
Workup
- additionmixing
- customreacted for 24 hours
- temperatureAfter the reaction mixture was cooled
- customfor quenching
- customthe reaction
- extractionto extract the product, and magnesium sulfate
- customAfter removing the solvent
- customthe residual was purified with column chromatography method
Sources & evidence
- ORD record
- ord-1dee1af4765542b787ac10036e0c472a
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08419808B2
Reaction notes
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