Ethanol → 4,4'-(Propane-1,2-diyl)bis{1-[(morpholin-4-yl)methyl]piperazine-2,6-dione}

HRID 648931Notes

Reaction equation

HRID 648931 reaction equation
O=[C:2]1[NH:7][C:6](=[O:8])[CH2:5][N:4]([CH2:9][CH:10]([N:12]2[CH2:17][C:16](=[O:18])[NH:15][C:14](=[O:19])[CH2:13]2)[CH3:11])[CH2:3]1.[NH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.[CH2:26]=[O:27].[CH2:28]([OH:30])[CH3:29]>>[CH3:11][CH:10]([N:12]1[CH2:17][C:16](=[O:18])[N:15]([CH2:5][N:4]2[CH2:3][CH2:2][O:30][CH2:28][CH2:29]2)[C:14](=[O:19])[CH2:13]1)[CH2:9][N:4]1[CH2:5][C:6](=[O:8])[N:7]([CH2:2][N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[C:26](=[O:27])[CH2:3]1

Participants

5

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 8083MorpholineHCID 30623Razoxane

Product 1

HCID 1256104,4'-(Propane-1,2-diyl)bis{1-[(morpholin-4-yl)methyl]piperazine-2,6-dione}Yield 84.9%

Procedure

A mixture of dl-1,2-bis(3,5-dioxopiperazin-1-yl)-propane (26.8 g, 0.1 mole), morpholine (27 ml, 0.3 mole) and absolute ethanol (100 ml) was heated to reflux. To the mixture, 37% aqueous formaldehyde solution (27 ml) was added gradually and then the reaction mixture was refluxed for further 15 minutes. The cooled mixture was filtered and the filtrate was allowed to stand in the refrigerator. Then resulting white crystals were collected and washed with ethyl acetate to give the titled compound (39.6 g; yield 84.9%).

Workup

  1. temperaturewas heated to reflux
  2. temperaturethe reaction mixture was refluxed for further 15 minutes
  3. filtrationThe cooled mixture was filtered
  4. customThen resulting white crystals
  5. customwere collected
  6. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-d0ad56a812fc4526adaffdc2429b8f3b
Source dataset
uspto-grants-1988_04
Patent number
US04737497

Reaction notes

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