HCID 20696425, compound → HCID 18362848, compound

HRID 381385Notes

Reaction equation

HRID 381385 reaction equation
CO[C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][OH:20])[CH2:14][CH2:13]2)=[O:11])=[N:6][CH:5]=1>CO.C(CN)O>[OH:11][CH2:10][CH2:7][NH:6][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([N:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][OH:20])[CH2:16][CH2:17]2)=[O:11])=[N:6][CH:5]=1

Participants

4

Reactant 1

HCID 20696425HCID 20696425, compound

Product 1

HCID 18362848HCID 18362848, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 700EthanolamineSolventHCID 887MethanolSolvent

Procedure

6-[1-(2-hydroxyethyl)piperazin-4-yl-carbonyl]nicotinic acid methyl ester (2 g) was dissolved in methanol (20 ml) and with the addition of ethanolamine (2 ml), the mixture was heated to reflux for 8 hours and concentrated under reduced pressure. The concentrated residue was dissolved in isopropanol (14 ml), and with the addition of isopropyl ether to precipitate. After 2-hours stirring, the filtered solid was recrystallized with ethyl acetate and hexane to give a desired compound of 1.74 g (yield: 79%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 8 hours
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe concentrated residue was dissolved in isopropanol (14 ml)
  5. additionwith the addition of isopropyl ether
  6. customto precipitate
  7. customthe filtered solid was recrystallized with ethyl acetate and hexane

Sources & evidence

ORD record
ord-b486eb215e56465aba92655fc9e6a05b
Source dataset
uspto-grants-2001_10
Patent number
US06306860B1

Reaction notes

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