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

HRID 1003305Notes

Reaction equation

HRID 1003305 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]([O-:17])=O)=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)[CH3:2].[K+].[NH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][OH:32].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl>[OH:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][NH:19][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:17]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 518202012-Amino-1-dodecanolHCID 23663822Potassium 6-(4-ethyl-1-piperazinyl)pyridine-3-carboxylate

Product 1

HCID 15462624N-(12-hydroxydodecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamideYield 81.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To 4.07 g of potassium 6-(4-ethyl-1-piperazinyl)-pyridine-3-carboxylate and 3.00 g of 12-aminododecanol was added 50 ml of chloroform and then 2.01 g of 1-hydroxybenzotriazole (HOBt) and 3.07 g of 1,3-dicyclohexylcarbodiimide (DCC) were added thereto while stirring at room temperature and then the mixture was stirred at room temperature for 17 hours. A further 50 ml of chloroform was added, the mixture was stirred and then insolubles were filtered off. After the residue on a filter paper was washed with chloroform, the washing and the chloroform solution were combined and washed with a 10% aqueous solution of sodium hydroxide and dried over anhydrous magnesium sulfate. After the chloroform solution was concentrated, diisopropyl ether was added and the crystal thus separated out was recovered by filtration and dried under reduced pressure to afford 5.10 g of the title compound as a crystal.

Workup

  1. stirringthe mixture was stirred at room temperature for 17 hours
  2. stirringthe mixture was stirred
  3. filtrationinsolubles were filtered off
  4. washAfter the residue on a filter paper was washed with chloroform
  5. washwashed with a 10% aqueous solution of sodium hydroxide
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationAfter the chloroform solution was concentrated
  8. additiondiisopropyl ether was added
  9. customthe crystal thus separated out
  10. filtrationwas recovered by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-2cb98e0d579245e9b2224c7ee0171304
Source dataset
uspto-grants-2000_04
Patent number
US06046201

Reaction notes

Loading…