Hydrogen Bromide → N-(12-Bromododecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide

HRID 1003294Notes

Reaction equation

HRID 1003294 reaction equation
O[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].[BrH:31]>C1(C)C=CC=CC=1>[Br:31][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]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 15462624N-(12-hydroxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide

Product 1

HCID 15462631N-(12-Bromododecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 419 mg of N-(12-hydroxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide in 20 ml of toluene was added 0.60 ml of a 47% hydrobromic acid and the mixture was heated under reflux for one hour. The reaction solution was washed successively with water, a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, 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 400 mg of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for one hour
  3. washThe reaction solution was washed successively with water
  4. dry with materiala saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue thus obtained
  7. customwas chromatographed over a silica gel column

Sources & evidence

ORD record
ord-39d1eaa0b02c4bc4b73f404b91c3c896
Source dataset
uspto-grants-2000_04
Patent number
US06046201

Reaction notes

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