Nicotinoyl chloride → HCID 13532765, compound

HRID 1906262Notes

Reaction equation

HRID 1906262 reaction equation
[OH:1][CH2:2][N:3]1[C:8](=[O:9])[CH2:7][N:6]([CH2:10][CH2:11][N:12]2[CH2:17][C:16](=[O:18])[N:15]([CH2:19][OH:20])[C:14](=[O:21])[CH2:13]2)[CH2:5][C:4]1=[O:22].[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29](Cl)=[O:30])[CH:24]=1>N1C=CC=CC=1>[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([O:20][CH2:19][N:15]2[C:14](=[O:21])[CH2:13][N:12]([CH2:11][CH2:10][N:6]3[CH2:7][C:8](=[O:9])[N:3]([CH2:2][O:1][C:29]([C:25]4[CH:24]=[N:23][CH:28]=[CH:27][CH:26]=4)=[O:30])[C:4](=[O:22])[CH2:5]3)[CH2:17][C:16]2=[O:18])=[O:30])[CH:24]=1

Participants

4

Reactant 2

HCID 82604Nicotinoyl chlorideHCID 13532751HCID 13532751, compound

Product 1

HCID 13532765HCID 13532765, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1,2-bis(4-hydroxymethyl-3,5-dioxopiperazin-1-yl)ethane (0.31 g, 1.0 m mol), 3-pyridylcarbonyl chloride (0.28 g, 2.0 m mol) and pyridine (10 ml) was stirred for 18 hours at room temperature. The solvent was removed from the reaction mixture under reduced pressure and the residue was extracted with chloroform. The extract solution was washed with saturated sodium bicarbonate aqueous solution successively with water, and was dried over magnesium sulfate. The residue obtained by removing the solvent under reduced pressure from the extract solution was purified by silica gel column chromatography (chloroform:ether:methanol=6:1:1, Rf value=0.3) to give the titled compound (0.12 g; yield 24%).

Workup

  1. customThe solvent was removed from the reaction mixture under reduced pressure
  2. extractionthe residue was extracted with chloroform
  3. washThe extract solution was washed with saturated sodium bicarbonate aqueous solution successively with water
  4. dry with materialwas dried over magnesium sulfate
  5. customThe residue obtained
  6. customby removing the solvent under reduced pressure from the extract solution
  7. customwas purified by silica gel column chromatography (chloroform:ether:methanol=6:1:1, Rf value=0.3)

Sources & evidence

ORD record
ord-35cac5ffeb3b4e8da37a1548388ca858
Source dataset
uspto-grants-1987_03
Patent number
US04650799

Reaction notes

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