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

HRID 1003295Notes

Reaction equation

HRID 1003295 reaction equation
I.[I:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH2:15].[CH2:16]([N:18]1[CH2:23][CH2:22][N:21]([C:24]2[N:29]=[CH:28][C:27]([C:30]([O-])=[O:31])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1)[CH3:17].[Na+].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1>C(Cl)Cl>[I:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][NH:15][C:30]([C:27]1[CH:28]=[N:29][C:24]([N:21]2[CH2:20][CH2:19][N:18]([CH2:16][CH3:17])[CH2:23][CH2:22]2)=[CH:25][CH:26]=1)=[O:31]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 1879642712-Iodododecylamine hydroiodideHCID 23663821Sodium 6-(4-ethylpiperazinyl)pyridine-3-carboxylate

Product 1

HCID 15462630N-(12-Iodododecyl)-6-(4-ethyl-1-piperazinyl)pyridine-3-carboxamideYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 170 mg of 12-iodododecylamine hydroiodide were added 120 mg of sodium 6-(4-ethyl-1-piperazinyl)-pyridine-3-carboxylate, 10 ml of methylene chloride, 95 mg of 1,3-dicyclohexylcarbodiimide (DCC) and 12 mg of 1-hydroxybenzotriazole (HOBt) and the mixture was stirred at room temperature for 3 hours. Insolubles were filtered off and the filtrate was chromatographed over a silica gel column to afford 169.5 mg of the title compound.

Workup

  1. filtrationInsolubles were filtered off
  2. customthe filtrate was chromatographed over a silica gel column

Sources & evidence

ORD record
ord-3c7d15cbda4a4f7a90e4db58bf0ba3d8
Source dataset
uspto-grants-2000_04
Patent number
US06046201

Reaction notes

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