Piperidinium acetate → HCID 178518156, compound
Reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH:12]=O)[CH2:8][CH2:7]1.[OH:24][CH:25]([CH2:34][OH:35])[CH2:26][NH:27][C:28]1[CH2:32][S:31][C:30](=[O:33])[N:29]=1.C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[F:23][C:2]([F:1])([F:22])[C:3]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[CH:14][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9](/[CH:12]=[C:32]2/[C:28]([NH:27][CH2:26][CH:25]([OH:24])[CH2:34][OH:35])=[N:29][C:30](=[O:33])[S:31]/2)[CH2:8][CH2:7]1Participants
5
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 1-[2,4-bis(trifluoromethyl)benzyl]piperidine-4-carbaldehyde (1.86 g) in 2-propanol (20 mL) were added 4-[(2,3-dihydroxypropyl)amino]-1,3-thiazol-2(5H)-one (1.56 g) and piperidinium acetate (0.794 g). The reaction mixture was stirred at 80° C. for 1 hr, and the solvent was evaporated under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol/ethyl acetate) and recrystallized from ethyl acetate/heptane to give the title compound (1.22 g).
Workup
- customthe solvent was evaporated under reduced pressure
- additionWater was added to the residue
- extractionthe mixture was extracted with ethyl acetate
- washThe extract was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel column chromatography (methanol/ethyl acetate)
- customrecrystallized from ethyl acetate/heptane
Sources & evidence
- ORD record
- ord-7e9c7bcc6d2b4c0abae84c5da398f9b7
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08772277B2
Reaction notes
Loading…