Ammonia → N,N'-bis(octoxycarbonylaminoneopentyl)piperazine

HRID 615273

Reaction equation

HRID 615273 reaction equation
[CH3:1][C:2]([CH3:18])([CH2:16]N)[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]([CH3:15])([CH3:14])[CH2:12]N)[CH2:6][CH2:5]1.[C:19](=[O:30])([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[NH2:20].[NH3:31]>C(O)CCCCCCC>[CH2:22]([O:21][C:19]([NH:20][CH:3]([N:4]1[CH2:9][CH2:8][N:7]([CH:10]([NH:31][C:19]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[O:30])[C:11]([CH3:15])([CH3:14])[CH3:12])[CH2:6][CH2:5]1)[C:2]([CH3:18])([CH3:16])[CH3:1])=[O:30])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 16240Carbamic acid, octyl esterHCID 20031516N,N'-bis(2,2-dimethyl-3-aminopropyl)piperazine

Product 1

HCID 20429701N,N'-bis(octoxycarbonylaminoneopentyl)piperazine

Reagents, catalysts & solvents 1

HCID 9571-OctanolSolvent

Procedure

Agitated in a reaction vessel are 256 parts of N,N'-bis(2,2-dimethyl-3-aminopropyl)piperazine with 400 parts of O-octyl carbamate and 130 parts of n-octanol at a reflux temperature of 190° C.-200° C. for 1 hour while the ammonia is removed by distillation. At that point, an additional 650 parts of n-octanol are allowed to flow into the reaction mixture and the reaction is continued at reflux temperature for 7 hours. Unreacted octanol and O-octylcarbonate are removed by distillation up to a sump temperature of 180° C.-200° C. at 2 millibars. By transcrystallization of the residue from acetone/water, 506 parts of N,N'-bis(octoxycarbonylaminoneopentyl)piperazine, C32H64N4O4 (molecular weight 568), are obtained corresponding with 89 percent of theory relative to N,N'-bis(2,2-dimethyl-3-aminopropyl)piperaxine. The melting point is 66° C.-68° C.

Workup

  1. customat a reflux temperature of 190° C.-200° C.
  2. customfor 1 hour
  3. customis removed by distillation
  4. temperatureat reflux temperature for 7 hours
  5. customare removed by distillation up to a sump temperature of 180° C.-200° C. at 2 millibars

Sources & evidence

ORD record
ord-cbff6c233fa1441c9da0a8759997e908
Source dataset
uspto-grants-1985_02
Patent number
US04497963

Linked notes

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