Water → HCID 59909615, compound
Reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[C@@H:11]([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)[CH2:10][CH2:9][NH:8][CH2:7]1)(=[O:3])[CH3:2].C(N(CC)CC)C.[F:28][C:29]1[CH:37]=[CH:36][C:32]([CH2:33][CH2:34]Br)=[CH:31][CH:30]=1.O>CN(C)C=O.CO>[F:28][C:29]1[CH:37]=[CH:36][C:32]([CH2:33][CH2:34][N:8]2[CH2:9][CH2:10][C@H:11]([N:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH2:14][CH2:13]3)[C@H:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH2:7]2)=[CH:31][CH:30]=1Participants
Conditions
- Temperature
- 50 °C
Procedure
cis-1-(3-Acetoxymethylpiperidin-4-yl)indoline (280 mg) was dissolved in dimethylformamide (4 ml) and methanol (1 ml). To the resultant solution were added triethylamine (222 mg) and 4-fluorophenethyl bromide (285 mg) followed by stirring at 50° C. for 2 hr. Then the reaction mixture was cooled and water (50 ml) was added thereto. After extracting with ether (50 ml) twice, the organic phase was washed with water (20 ml) twice and a 2 N aqueous solution (50 ml) of sodium hydroxide once and dried over anhydrous magnesium sulfate. Then the solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate system) to give the title compound (100 mg) as a colorless oil (yield: 28%).
Workup
- temperatureThen the reaction mixture was cooled
- extractionAfter extracting with ether (50 ml) twice
- washthe organic phase was washed with water (20 ml) twice
- dry with materiala 2 N aqueous solution (50 ml) of sodium hydroxide once and dried over anhydrous magnesium sulfate
- customThen the solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate system)
Sources & evidence
- ORD record
- ord-5bf9346edb7047869aa6abab44bb6ed5
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07071201B2
Reaction notes
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