2-Amino-2-methyl-1-propanol → 2,2,5,5-tetramethylpiperazine

HRID 1090754Notes

Reaction equation

HRID 1090754 reaction equation
[NH2:1][C:2]([CH3:6])([CH3:5])[CH2:3]O.[H][H]>COCCOCCOCCOCCOC>[CH3:5][C:2]1([CH3:6])[CH2:3][NH:1][C:2]([CH3:6])([CH3:3])[CH2:5][NH:1]1

Participants

4

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 178418361HCID 178418361, compound

Product 1

HCID 2255722,2,5,5-tetramethylpiperazineYield 62%

Reagents, catalysts & solvents 1

HCID 8925TetraglymeSolvent2×

Procedure

In this example, 139 cc of a Ni-Fe-Cu-Mn catalyst (1/8" diameter) were charged to an 0.815" ID tubular upward flow reactor. A liquid feed containing 2-amino-2-methyl-1-propanol and tetraglyme (a tetraethylene glycol dimethyl ether solvent) (1/1.18 by weight) was pumped through the catalyst bed at a rate of 0.12 lb/hr at 240° C. Hydrogen was also passed through the reactor at a rate of about 6 L/hr. The pressure was maintained at 800 psig. The products were collected. GLC analysis showed that a 62% yield of 2,2,5,5-tetramethylpiperazine and a 14% yield of 3,3,6,6-tetramethyl-2-piperazinone were obtained with a 90% conversion of 2-amino-2-methyl-1-propanol. The resulting reaction mixture was fractionally distilled at atmospheric pressure under nitrogen. Both products were further recrystallized from ether.

Workup

  1. customwas pumped through the catalyst bed at a rate of 0.12 lb/hr at 240° C
  2. temperatureThe pressure was maintained at 800 psig
  3. customThe products were collected

Sources & evidence

ORD record
ord-9f3dd365655f4878a852362c8167eb77
Source dataset
uspto-grants-1992_01
Patent number
US05082917

Reaction notes

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