Triethylamine → HCID 11373410, compound

HRID 1860440Notes

Reaction equation

HRID 1860440 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH2:21][OH:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:30](Cl)(=[O:38])[O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH2:21][O:22][C:30]([O:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:38])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 10827800(1,4-Dibenzylpiperazin-2-yl)methanol

Product 1

HCID 11373410HCID 11373410, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution comprising 10 g (33.7 mmol) of 1,4-dibenzyl-2-hydroxymethylpiperazine (prepared in accordance with the process described by Jucker and Rissi in Helv. Chem. Acta, 1962, 45, 2383-2402) in 9.5 ml (2.8 equivalents; 94.4 mmol) of triethylamine and 95 ml of dichloromethane (CH2Cl2) is placed in a 500 ml ground-necked conical flask on which is fitted an addition funnel, and is cooled in an ice bath. After dropwise addition of 6.4 g (1.25 equivalents; 42 mmol) of phenyl chlorocarbonate dissolved in 95 ml of CH2Cl2, the mixture is stirred at 0° C. for one hour and then at room temperature for 10 hours. At the end of the reaction, the solution is washed once with saturated sodium bicarbonate (NaHCO3), solution and then with water until a neutral pH is obtained, and it is dried over magnesium sulfate (MgSO4). After filtration on paper and evaporation of the CH2Cl2, the residue is chromatographed on a column of silica gel, using dichloromethane as eluent. 8 g of 1,4-dibenzyl-2-phenoxycarbonyloxymethylpiperazine are thus obtained in the form of a viscous product. Yield: 57%. Rf=0.52 (2/98 v/v MeOH/CH2Cl2,).

Workup

  1. customprepared in accordance with the process
  2. customis fitted an addition funnel
  3. temperatureis cooled in an ice bath
  4. waitat room temperature for 10 hours
  5. customAt the end of the reaction
  6. washthe solution is washed once with saturated sodium bicarbonate (NaHCO3), solution
  7. customwith water until a neutral pH is obtained
  8. dry with materialit is dried over magnesium sulfate (MgSO4)
  9. filtrationAfter filtration
  10. customon paper and evaporation of the CH2Cl2
  11. customthe residue is chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-b59d79e7500a4ee789c7127dce09f3f0
Source dataset
uspto-grants-2003_03
Patent number
US06531476B1

Reaction notes

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