Ammonium Chloride → HCID 22678342, compound
Reaction equation
CON(CC)[C:4](=[O:21])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]2[C:14]([O:19][CH3:20])=[N:15][CH:16]=[CH:17][CH:18]=2)[CH2:8][CH2:7]1.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1[Li].[Cl-].[NH4+]>O1CCCC1>[CH3:20][O:19][C:14]1[C:13]([CH2:12][N:9]2[CH2:8][CH2:7][CH:6]([CH2:5][C:4](=[O:21])[C:25]3[S:24][CH:28]=[CH:27][CH:26]=3)[CH2:11][CH2:10]2)=[CH:18][CH:17]=[CH:16][N:15]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
0.50 g of N1-methoxy,N1-ethyl-2-[1-[(2-methoxy-3-pyridyl)methyl]-4-piperidyl]acetamide obtained in Example 55 was dissolved in 3 ml of tetrahydrofuran and 1.8 ml of a 1.0M (2-thienyl)-lithium in tetrahydrofuran was added dropwise thereinto at −78° C. After completion of the dropwise addition, the mixture was further stirred at −78° C. for 1 hour. An aqueous saturated ammonium chloride was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by silica gel column chromatography (ethyl acetate), to give 0.22 g of the title compound as a pale yellow oil. The NMR spectrum data of the title compound were agreed with those of Example 54.
Workup
- customat −78° C
- additionAfter completion of the dropwise addition
- extractionthe mixture was extracted with ethyl acetate
- washThe organic layer was washed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated
- customthe crude product was purified by silica gel column chromatography (ethyl acetate)
Sources & evidence
- ORD record
- ord-5bba70800c344d8693e173a06d30e1e4
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06784192B2
Reaction notes
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