Pyridine → N-(12-mesyloxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide

HRID 1003299Notes

Reaction equation

HRID 1003299 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(N(CC)CC)C.N1C=CC=CC=1.[S:44](Cl)([CH3:47])(=[O:46])=[O:45]>C(Cl)(Cl)Cl>[S:44]([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])([CH3:47])(=[O:46])=[O:45]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15462624N-(12-hydroxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide

Product 1

HCID 15462632N-(12-mesyloxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1.26 g of N-(12-hydroxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide in 20 ml of chloroform were added 4.2 ml of triethylamine, 5 ml of pyridine and 1.0 ml of mesyl chloride and the mixture was stirred at room temperature for 30 minutes. The reaction solution was washed successively with water, 3N-hydrochloric acid 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 1.11 g of the title compound.

Workup

  1. washThe reaction solution was washed successively with water, 3N-hydrochloric acid
  2. dry with materiala saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue thus obtained
  5. customwas chromatographed over a silica gel column

Sources & evidence

ORD record
ord-ce3abe527829467389083ae291fa2edd
Source dataset
uspto-grants-2000_04
Patent number
US06046201

Reaction notes

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