Acetone Cyanohydrin → 1,1'-Ethylenebis(4-acetyl-3,3,5,5-tetramethyl-2-piperazinone)

HRID 580600

Reaction equation

HRID 580600 reaction equation
[CH2:1]([N:14]1[CH2:19][C:18]([CH3:21])([CH3:20])[NH:17][C:16]([CH3:23])([CH3:22])[C:15]1=[O:24])[CH2:2][N:3]1[CH2:8][C:7]([CH3:10])([CH3:9])[NH:6][C:5]([CH3:12])([CH3:11])[C:4]1=[O:13].NC(C)(C)CNCCN.C[C:35](C)([OH:38])[C:36]#N.[C:40](OC(=O)C)(=[O:42])[CH3:41]>S(=O)(=O)(O)O.C(Cl)Cl>[CH2:2]([N:3]1[CH2:8][C:7]([CH3:9])([CH3:10])[N:6]([C:35](=[O:38])[CH3:36])[C:5]([CH3:12])([CH3:11])[C:4]1=[O:13])[CH2:1][N:14]1[CH2:19][C:18]([CH3:21])([CH3:20])[N:17]([C:40](=[O:42])[CH3:41])[C:16]([CH3:23])([CH3:22])[C:15]1=[O:24]

Participants

7

Reactant 4

HCID 6406Acetone CyanohydrinHCID 7918Acetic AnhydrideHCID 1169791,1'-Ethylenebis(3,3,5,5-tetramethylpiperazinone)HCID 10898752N,N'-(2-amino-2-methylpropyl)ethylenediamine

Product 1

HCID 201342741,1'-Ethylenebis(4-acetyl-3,3,5,5-tetramethyl-2-piperazinone)

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
130 °C

Procedure

31.5 grams (0.1 mole) of 1,1'-ethylenebis(3,3,5,5-tetramethyl-2-piperazinone), prepared according to Example 6, E of U.S. Pat. No. 4,190,571 from N,N'-(2-amino-2-methylpropyl)ethylenediamine and acetone cyanohydrin, is dissolved in 102 grams (1.0 mole) of acetic anhydride. After three drops of concentrated sulfuric acid are added to the solution, the mixture is heated for four hours at 130° C. and then cooled to room temperature. Methylene chloride (200 ml.) is added to extract the product into an organic layer which is then washed successively with water and with saturated sodium bicarbonate solution and is finally dried over anhydrous magnesium sulfate. The solvent is removed in vacuo and the residual product is recrystallized from toluene to give 30.4 grams of the above-named product as a white solid, melting at 180°-183° C. (sintering at 170° C.).

Workup

  1. temperaturecooled to room temperature
  2. extractionto extract the product into an organic layer which
  3. washis then washed successively with water and with saturated sodium bicarbonate solution
  4. dry with materialis finally dried over anhydrous magnesium sulfate
  5. customThe solvent is removed in vacuo
  6. customthe residual product is recrystallized from toluene

Sources & evidence

ORD record
ord-5f5b2198d01f437dbb080742b5a1763a
Source dataset
uspto-grants-1988_06
Patent number
US04753979

Linked notes

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