Pyridine → N-(12-Tosyloxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide
Reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([C:17]1[CH:18]=[N:19][C:20]([N:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH3:30])[CH2:25][CH2:24]2)=[CH:21][CH:22]=1)=[O:16].N1C=CC=CC=1.[S:37](Cl)([C:40]1[CH:46]=[CH:45][C:43]([CH3:44])=[CH:42][CH:41]=1)(=[O:39])=[O:38]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[S:37]([O:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([C:17]1[CH:18]=[N:19][C:20]([N:23]2[CH2:28][CH2:27][N:26]([CH2:29][CH3:30])[CH2:25][CH2:24]2)=[CH:21][CH:22]=1)=[O:16])([C:40]1[CH:46]=[CH:45][C:43]([CH3:44])=[CH:42][CH:41]=1)(=[O:39])=[O:38]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a suspension of 210 mg of N-(12-hydroxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide in 10 ml of methylene chloride were added 0.03 ml of pyridine, 115 mg of tosyl chloride and a catalytic amount of 4-dimethylaminopyridine and the mixture was stirred at room temperature for one hour. The reaction solution was washed with water and a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue thus obtained was chromatographed over a silica gel column to afford 219 mg of the title compound.
Workup
- washThe reaction solution was washed with water
- dry with materiala saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
- customthe residue thus obtained
- customwas chromatographed over a silica gel column
Sources & evidence
- ORD record
- ord-4f7a1027276546e9818b5c44e911e1fe
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06046201
Reaction notes
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