Acetone → 1,3,3,4-Tetramethylpiperazin-2-one

HRID 986340Notes

Reaction equation

HRID 986340 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][NH:5][CH3:6].[CH:7](Cl)(Cl)Cl.[CH3:11][C:12]([CH3:14])=O.[OH-:15].[Na+]>O.ClCCl>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([CH3:6])[C:12]([CH3:14])([CH3:7])[C:11]1=[O:15]

Participants

7

Reactant 4

HCID 180AcetoneHCID 6212ChloroformHCID 8070N,N'-DimethylethylenediamineHCID 14798Sodium Hydroxide

Product 1

HCID 180033511,3,3,4-Tetramethylpiperazin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

8.8 g N,N'-dimethyl-ethylene diamine, 12.0 g CHCl3, and 6.0 g acetone are placed in a 250 ml flask in an ice-bath, and 1.1 g BTAC added. To provide a homogeneous organic liquid phase, 100 ml dichloromethane is added. Then 40 ml conc NaOH (50% by wt) is dripped into the flask over about 30 mins. The reaction is allowed to proceed for about 5 hr and the reaction product is worked up by dissolving in a minimum amount of water, and then enough dichloromethane is added to provide two distinct layers. The aqueous layer is extracted twice with 50 ml dichloromethane, washed and worked up is a conventional manner. Upon distillation the product is obtained. The foregoing structure of the compound is supported by IR, NMR, GC and mass spectrometer data.

Workup

  1. addition1.1 g BTAC added
  2. additionis added
  3. customto provide two distinct layers
  4. extractionThe aqueous layer is extracted twice with 50 ml dichloromethane
  5. washwashed
  6. distillationUpon distillation the product
  7. customis obtained

Sources & evidence

ORD record
ord-e1a2a07c2e984f1b918b1b1ca1990dbc
Source dataset
uspto-grants-1987_12
Patent number
US04711957

Reaction notes

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