Potassium Carbonate → N-(12-hydroxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide

HRID 1003303Notes

Reaction equation

[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]([NH2:17])=[O:16])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][OH:39]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[OH:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][NH:17][C:15]([C:12]1[CH:13]=[N:14][C:9]([N:6]2[CH2:5][CH2:4][N:3]([CH2:1][CH3:2])[CH2:8][CH2:7]2)=[CH:10][CH:11]=1)=[O:16]

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of 0.055 g of 6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamide, 0.011 g of tetrabutylammonium hydrogen sulfate, 0.11 g of sodium hydroxide and 0.05 g of potassium carbonate in 3 ml of toluene was added dropwise at 70° C. a solution of 12-bromododecanol in 2 ml of toluene and the mixture was stirred at 70° C. for 13 hours. The reaction solution was diluted with chloroform, washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue thus obtained was chromatographed over a silica gel column to afford 0.025 g of the title compound.

Workup

washwashed with water
dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium 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-6ead61ed7f334ccbbe9f4b782457297e
Source dataset: uspto-grants-2000_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06046201

Reaction notes

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