2-Bromopropane → N-(12-Hydroxydodecyl)-6-(4-isopropyl-1-piperazinyl)pyridine-3-carboxamide

HRID 1003304Notes

Reaction equation

HRID 1003304 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][NH:26][CH2:25][CH2:24]2)=[CH:21][CH:22]=1)=[O:16].[CH:29](Br)([CH3:31])[CH3:30].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(Cl)(Cl)Cl>[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[CH2:24][CH2:25][N:26]([CH:29]([CH3:31])[CH3:30])[CH2:27][CH2:28]2)=[CH:21][CH:22]=1)=[O:16]

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 18796424N-(12-hydroxydodecyl)-6-(1-piperazinyl)pyridine-3-carboxamide

Product 1

HCID 15462626N-(12-Hydroxydodecyl)-6-(4-isopropyl-1-piperazinyl)pyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 0.7 g of N-(12-hydroxydodecyl)-6-(1-piperazinyl)pyridine-3-carboxamide, 0.24 g of isopropyl bromide and 0.7 g of potassium carbonate in 20 ml of dimethylformamide was stirred at 100° C. for 3 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 the title compound as a crystal.

Workup

  1. washwashed with water
  2. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium 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-fdfa2ac44cd84b5da77bd1f6e8da6666
Source dataset
uspto-grants-2000_04
Patent number
US06046201

Reaction notes

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