Triethylamine → 3-Oxo-butyric acid 4-cyclohexylpiperazide

HRID 580510Notes

Reaction equation

HRID 580510 reaction equation
[CH:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:20]=[C:21]1[O:25][C:23](=[O:24])[CH2:22]1>O1CCCC1>[CH:1]1([N:7]2[CH2:12][CH2:11][N:10]([C:23](=[O:24])[CH2:22][C:21](=[O:25])[CH3:20])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12661DiketeneHCID 872981-Cyclohexylpiperazine

Product 1

HCID 861624823-Oxo-butyric acid 4-cyclohexylpiperazide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

24 g (0.1 mol) of 1-cyclohexylpiperazine are suspended in 150 ml of absolute tetrahydrofuran. 20 ml of triethylamine are poured in and, after 20 minutes, 18.6 g of diketene in 20 ml of tetrahydrofuran are added dropwise, and the mixture is then stirred at room temperature for 2 h. Thereafter part of the solvent is removed by distillation in vacuo, the mixture is poured onto 200 ml of ice-water, 20 g of Na2CO3 are added, and extraction is carried out 3 times with 50 ml of methylene chloride each time. After the organic phase has been dried with MgSO4, crude 3-oxo-butyric acid 4-cyclohexylpiperazide is obtained as the residue from evaporation.

Workup

  1. customThereafter part of the solvent is removed by distillation in vacuo
  2. additionthe mixture is poured onto 200 ml of ice-water, 20 g of Na2CO3
  3. additionare added
  4. extractionextraction
  5. dry with materialAfter the organic phase has been dried with MgSO4

Sources & evidence

ORD record
ord-a39a501e88c040eabb6bfa8369c1b2dc
Source dataset
uspto-grants-1988_06
Patent number
US04753936

Reaction notes

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