1-Methylpiperazine → HCID 178418611, compound

HRID 5521Notes

Reaction equation

HRID 5521 reaction equation
CO[C:3]([C:5]1[CH:10]=[C:9]([OH:11])[C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:7][N:6]=1)=[O:4].[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>C(Cl)(Cl)Cl.CO>[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:3]([C:5]2[CH:10]=[C:9]([OH:11])[C:8]([O:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[CH:7][N:6]=2)=[O:4])[CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 531671-MethylpiperazineHCID 178418684HCID 178418684, compound

Product 1

HCID 178418611HCID 178418611, compoundYield 17.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 2-methoxycarbonyl-4-hydroxy-5-benzyloxypyridine (18.15 g) in N-methylpiperazine (21.04 g) was heated to 100° C. for 3.5 hours. The resulting viscous solution was cooled to room temperature, diluted with a mixture of chloroform (270 ml) and methanol (30 ml) and subjected to column chromatography on silica gel (800 g). The eluate was evaporated in vacuo and the residue was purified by column chromatography on silica gel (600 g). The pure fractions were evaporated in vacuo and the residue was pulverized with diisopropyl ether to give 1-methyl-4-(4-hydroxy-5-benzyloxy-2-pyridylcarbonyl)piperazine (3.99 g).

Workup

  1. temperatureThe resulting viscous solution was cooled to room temperature
  2. customThe eluate was evaporated in vacuo
  3. customthe residue was purified by column chromatography on silica gel (600 g)
  4. customThe pure fractions were evaporated in vacuo

Sources & evidence

ORD record
ord-267ddbce90734d2f82315bf163cec8db
Source dataset
uspto-grants-1993_09
Patent number
US05244890

Reaction notes

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