Piperidine → 2-cyano-3-[5-(7-dibutylamino-9H-fluoren-2-yl)-thiophen-2-yl]-acrylic acid
Reaction equation
[CH2:1]([N:5]([CH2:26][CH2:27][CH2:28][CH3:29])[C:6]1[CH:18]=[C:17]2[C:9]([C:10]3[CH:11]=[CH:12][C:13]([C:19]4[S:23][C:22]([CH:24]=O)=[CH:21][CH:20]=4)=[CH:14][C:15]=3[CH2:16]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[C:30]([CH2:32][C:33]([OH:35])=[O:34])#[N:31].N1CCCCC1>C(#N)C>[C:30]([C:32](=[CH:24][C:22]1[S:23][C:19]([C:13]2[CH:12]=[CH:11][C:10]3[C:9]4[C:17](=[CH:18][C:6]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:26][CH2:27][CH2:28][CH3:29])=[CH:7][CH:8]=4)[CH2:16][C:15]=3[CH:14]=2)=[CH:20][CH:21]=1)[C:33]([OH:35])=[O:34])#[N:31]Participants
Conditions
- Temperature
- 90 °C
Procedure
Under N2 atmosphere, 0.18 parts of 5-(7-dibutylamino-9H-fluoren-2-yl)-thiophene-2-carbaldehyde (12a), 0.05 parts of cyanoacetic acid, and 0.017 parts of piperidine were added into acetonitrile, followed by stirring and mixing. Then, the reaction mixture was heated to 90° C. and reacted for 6 hours. After the reaction mixture was cooled to room temperature, the reaction mixture was filtrated to obtain a solid. Then, the solid was washed with water, ether, and acetonitrile sequentially to obtain a dark red solid. Finally, this crude was purified with column chromatography method by using dichloromethane/methanol co-solvent as an eluent, to obtain a compound (13a) of the present example. This compound was in a form of a dark red solid, and the yield of this compound was 73%.
Workup
- additionmixing
- customreacted for 6 hours
- temperatureAfter the reaction mixture was cooled to room temperature
- filtrationthe reaction mixture was filtrated
- customto obtain a solid
- washThen, the solid was washed with water, ether, and acetonitrile sequentially
- customto obtain a dark red solid
- customFinally, this crude was purified with column chromatography method
Sources & evidence
- ORD record
- ord-08b9b57452ec417c83c96c71f031521e
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08203068B2
Reaction notes
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