Reaction equation
[CH2:1]([Li])CCC.[S:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[C:15]([CH:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)[CH2:19][CH2:18]1)=O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1.CCCCCC>[CH3:32][O:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][CH2:23][N:20]2[CH2:21][CH2:22][CH:17]([C:15]([C:7]3[S:6][C:10]4[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=4[N:8]=3)=[CH2:1])[CH2:18][CH2:19]2)=[CH:26][CH:27]=1Participants
6
Reactant 2
Product 1
Reagents, catalysts & solvents 3
Procedure
Dissolve methyltriphenylphosphonium bromide (2.50 g, 6.99 mmol) in anhydrous tetrahydrofuran (50 mL). Add n-butyllithium (2.8 mL of a 2.5M solution in hexane, 6.99 mmol) and cool to -10° C. Add, by dropwise addition, a solution of [2-benzothiazolyl][1-[2-(4-methoxyphenyl)ethyl]-4-piperidinyl]methanone (2.66 g, 6.99 mmol) in anhydrous tetrahydrofuran (50 mL). Stir for 2 hours then quench with water. Separate the organic phase and extract the aqueous phase with ethyl ether. Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (50% ethyl ether/hexane) to give the title compound as a white powder; mp 84°-85° C.
Workup
- additionAdd, by dropwise addition
- customthen quench with water
- customSeparate the organic phase
- extractionextract the aqueous phase with ethyl ether
- dry with materialdry (MgSO4)
- customevaporate the solvent in vacuo
- customPurify by chromatography (50% ethyl ether/hexane)
Sources & evidence
- ORD record
- ord-82efebb1b002442897526beaadb37e17
- Source dataset
- uspto-grants-1997_07
- Patent number
- US05650416
Linked notes
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