4-(4-Diisopropylaminomethylbenzoyl)-1-tritylpiperidine → 4-(4-Diisopropylaminomethylbenzoyl)piperidine
Reaction equation
[CH:1]([N:4]([CH2:8][C:9]1[CH:41]=[CH:40][C:12]([C:13]([CH:15]2[CH2:20][CH2:19][N:18](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:17][CH2:16]2)=[O:14])=[CH:11][CH:10]=1)[CH:5]([CH3:7])[CH3:6])([CH3:3])[CH3:2]>C(O)(=O)C>[CH:1]([N:4]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[O:14])=[CH:40][CH:41]=1)[CH:5]([CH3:7])[CH3:6])([CH3:2])[CH3:3]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 4-(4-diisopropylaminomethylbenzoyl)-1-tritylpiperidine (1.3 g) and 80% acetic acid aqueous solution (20 ml) was stirred at 80° C. for 1 hour and concentrated. To the residue was added water, and the solution was extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated to give an oil of 4-(4-diisopropylaminomethylbenzoyl)piperidine (1.0 g). To a solution of the oil (302 mg) in THF (10 ml) was added 6-chloronaphthalene-2-sulfonylchloride (261 mg), and the mixture was stirred at room temperature for 1 hour. To the mixture was added sodium hydrogen carbonate aqueous solution, and the mixture was extracted with ethyl acetate. The extract was washed with water, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography and eluted with hexane-ethyl acetate (4:1) to give the title compound (0.15g).
Workup
- concentrationconcentrated
- additionTo the residue was added water
- extractionthe solution was extracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-131a4c63a0dc4ee9ae01e5dc1722fb06
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06359134B1
Reaction notes
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