(E)-6-methoxy-5-(4-methylpiperidin-1-yl)-2-(3-(trifluoromethyl)benzylidene)-2,3-dihydro-1H-inden-1-one → 6-methoxy-5-(4-methylpiperidin-1-yl)-2-(3-(trifluoromethyl) benzyl)-2,3-dihydro-1H-inden-1-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7]/[C:8](=[CH:13]\[C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)/[C:9]2=[O:12])=[CH:5][C:4]=1[N:24]1[CH2:29][CH2:28][CH:27]([CH3:30])[CH2:26][CH2:25]1>CO.[Ni]>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH:8]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=3)[C:9]2=[O:12])=[CH:5][C:4]=1[N:24]1[CH2:29][CH2:28][CH:27]([CH3:30])[CH2:26][CH2:25]1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
The 153 (100 mg, 0.240 mmol) was dissolved in methanol and Raney-Nickel (10 mg, 10% v/v) added and the reaction stirred under hydrogen balloon for 6 h. The reaction was filtered through celite bed and washed with excess methanol. The organic layer was concentrated to get the crude compound 154 which was purified by flash chromatography using 100-200 mesh silica gel. The compound 154 was eluted at 20% ethyl acetate in hexane as half white coloured solid compound 6-methoxy-5-(4-methylpiperidin-1-yl)-2-(3-(trifluoromethyl)benzyl)-2,3-dihydro-1H-inden-1-one 154. 1HNMR (400 MHz, CDCl3) δ ppm 7.40 (m, 4H), 7.15 (s, 1H), 6.82 (s, 1H), 3.89 (s, 3H), 3.60 (s, 2H), 3.41 (dd, 1H), 2.94 (m, 2H), 2.62 (m, 4H), 0.92 (m, 4H), 0.85 (m, 3H); MS (ESI) m/z 418.0 (M+H).
Workup
- filtrationThe reaction was filtered through celite bed
- washwashed with excess methanol
- concentrationThe organic layer was concentrated
Sources & evidence
- ORD record
- ord-649243353cdb44e496dcffe68d6823c2
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09446047B2
Reaction notes
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