Benzylamine → 1-Benzyl-4-tert-butyl-piperazine

HRID 1657753

Reaction equation

HRID 1657753 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:9][CH2:10]Cl)[C:5]([CH3:8])([CH3:7])[CH3:6].[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[CH2:12]([N:19]1[CH2:10][CH2:9][N:4]([C:5]([CH3:8])([CH3:7])[CH3:6])[CH2:3][CH2:2]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 96167Triethylamine, 2',2''-dichloro-1,1-dimethyl-

Product 1

HCID 35919371-Benzyl-4-tert-butyl-piperazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of 2000 g of bis-(2-chloroethyl)-tert-butylamine in 500 cc of ethanol and a solution of 1095 g of benzylamine in 750 cc of ethanol are simultaneously added dropwise to 1000 cc of boiling ethanol. After the addition is complete, the reaction mixture is heated to the boil for 1 hour. The mixture is subsequently concentrated in a vacuum and the residue is dissolved in dilute hydrochloric acid. The acid solution is washed with ether and is subsequently rendered alkaline with a concentrated, aqueous sodium hydroxide solution. The liberated base is extracted with ether and the ether residue is distilled. 1-benzyl-4-tert-butyl piperazine has a B.P. of 160°-162° at 12 mm of Hg.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture is heated to the boil for 1 hour
  3. concentrationThe mixture is subsequently concentrated in a vacuum
  4. dissolutionthe residue is dissolved in dilute hydrochloric acid
  5. washThe acid solution is washed with ether
  6. extractionThe liberated base is extracted with ether
  7. distillationthe ether residue is distilled

Sources & evidence

ORD record
ord-b0a805842af4428eaa3f82b69830ea24
Source dataset
uspto-grants-1976_06
Patent number
US03962248

Linked notes

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