Nitric Acid → N-(12-Nitroxydodecyl)-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].C(=O)([O-])O.[Na+].[N+:36]([O-])([OH:38])=[O: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])[N+:36]([O-:38])=[O:37]Participants
4
Conditions
- Temperature
- -25 °C
Procedure
To 30 ml of fuming nitric acid cooled to -30° C. was gradually added 7.9 g of N-(12-hydroxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide over 30 minutes and the mixture was stirred at -30 to -20° C. for 40 minutes. The reaction solution was poured into ice, neutralized with sodium hydrogen carbonate and extracted with chloroform. The extract was dried over anhydrous sodium sulfate and distilled under reduced pressure. The residue thus obtained was chromatographed over a silica gel column and recystallized from methanol-water to afford the title compound as a crystal.
Workup
- customover 30 minutes
- additionThe reaction solution was poured into ice
- extractionextracted with chloroform
- dry with materialThe extract was dried over anhydrous sodium sulfate
- distillationdistilled under reduced pressure
- customThe residue thus obtained
- customwas chromatographed over a silica gel column
Sources & evidence
- ORD record
- ord-4434ce0158344e0893e54d00fe7dad14
- Source dataset
- uspto-grants-2000_04
- Patent number
- US06046201
Reaction notes
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