Morpholine → 2-[4-(2-hydroxyethyl)piperazin-1-yl]-N-[2,4-bis(morpholino)-6-methylpyridin-3-yl]acetamide

HRID 227520Notes

Reaction equation

HRID 227520 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl[C:8]1[C:13]([NH:14][C:15](=[O:26])[CH2:16][N:17]2[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][OH:25])[CH2:19][CH2:18]2)=[C:12](Cl)[CH:11]=[C:10]([CH3:28])[N:9]=1>>[OH:25][CH2:24][CH2:23][N:20]1[CH2:21][CH2:22][N:17]([CH2:16][C:15]([NH:14][C:13]2[C:8]([N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[N:9][C:10]([CH3:28])=[CH:11][C:12]=2[N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:26])[CH2:18][CH2:19]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 10020570N-(2,4-dichloro-6-methylpyridin-3-yl)-2-[4-(2-hydroxyethyl)piperazin-1-yl]acetamide

Product 1

HCID 210873422-[4-(2-hydroxyethyl)piperazin-1-yl]-N-[2,4-bis(morpholino)-6-methylpyridin-3-yl]acetamideYield 63.9%

Conditions

Temperature
100 °C

Procedure

Morpholine (9.0 mL) was added to N-(2,4-dichloro-6- methylpyridin-3-yl)-2-[4-(2-hydroxyethyl)piperazin-1-yl]acetamide (1.0 g, 2.88 mmol), and the mixture was stirred for 24 hours at 100° C. The reaction mixture was allowed to cool and concentrated under reduced pressure. The residue was purified through silica gel column chromatography (developer: chloroform/ammonia-saturated methanol=50/1), to thereby yield 826 mg of 2-[4-(2-hydroxyethyl)piperazin-1-yl]-N-[2,4-bis(morpholino)-6-methylpyridin-3-yl]acetamide in a yellow amorphous state (yield: 63.9%).

Workup

  1. temperatureto cool
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified through silica gel column chromatography (developer: chloroform/ammonia-saturated methanol=50/1)

Sources & evidence

ORD record
ord-0abb4d1153d543c890956a6b00c159a6
Source dataset
uspto-grants-2009_07
Patent number
US07560547B2

Reaction notes

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