1-Hydroxybenzotriazole → N-(12-Nitroxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide

HRID 1003291Notes

Reaction equation

HRID 1003291 reaction equation
Cl.[N+:2]([O-:18])([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])=[O:3].[CH2:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27]2[N:32]=[CH:31][C:30]([C:33]([O-])=[O:34])=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)[CH3:20].[Na+].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.C(Cl)(Cl)Cl>[O:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:33]([C:30]1[CH:31]=[N:32][C:27]([N:24]2[CH2:23][CH2:22][N:21]([CH2:19][CH3:20])[CH2:26][CH2:25]2)=[CH:28][CH:29]=1)=[O:34])[N+:2]([O-:18])=[O:3]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 1879641612-Aminododecyl nitrate hydrochlorideHCID 23663821Sodium 6-(4-ethylpiperazinyl)pyridine-3-carboxylate

Product 1

HCID 15462625N-(12-Nitroxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamideYield 91.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.7 g of 12-aminododecyl nitrate hydrochloride in 80 ml of methylene chloride were added successively under ice-cooling 5.21 g of sodium 6-(4-ethylpiperazinyl)pyridine-3-carboxylate, 3.91 g of 1-hydroxybenzotriazole (HOBt) and 2.76 g of 1-ethyl-3-(3-dimethylaminopropyl )carbodiimide hydrochloride (WSCI) and then the mixture was stirred at room temperature overnight. The reaction solution was diluted with chloroform and washed successively with water, a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and then distilled under reduced pressure. The residue thus obtained was chromatographed over a silica gel column to afford 8.56 g of the title compound as a crystal.

Workup

  1. washwashed successively with water
  2. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  3. distillationdistilled under reduced pressure
  4. customThe residue thus obtained
  5. customwas chromatographed over a silica gel column

Sources & evidence

ORD record
ord-80eca58785924159938dc19ae49d1c03
Source dataset
uspto-grants-2000_04
Patent number
US06046201

Reaction notes

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