Ethanol → HCID 10738521, compound

HRID 1860448Notes

Reaction equation

HRID 1860448 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][NH2:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:30][C:31]([CH3:36])([CH3:35])[C:32](Cl)=[O:33].C(O)C>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][NH:22][C:32]([C:31]([CH3:36])([CH3:35])[CH3:30])=[O:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 10085886HCID 10085886, compound

Product 1

HCID 10738521HCID 10738521, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.36 g (13.1 mmol) of 1,4-dibenzyl-2-aminomethylpiperazine prepared according to a protocol identical to the one used in steps 6.1 and 6.2 of Example 6 are dissolved in 5.5 ml (3 equivalents; 39.3 mmol) of triethylamine and 100 ml of dichloromethane and are treated by rapid dropwise addition of 2.63 ml (1.5 equivalents; 19.6 mmol) of 2,2-dimethylpropanoyl chloride dissolved in 30 ml of CH2Cl2. The solution is refluxed for 4 hours. A few ml of ethanol are then added, after which the solution is washed twice with water, once with saturated NaHCO3 solution and then with water until a neutral pH is obtained. After drying the organic phase (MgSO4), filtration on paper and evaporation of the solvents, the residue is chromatographed on a column of silica gel, eluting with an MeOH/CH2Cl2 mixture (0.5/99.5 v/v). 2.44 g of 1,4-dibenzyl-2-tert-butylcarbonylaminomethylpiperazine are thus obtained in the form of a viscous product. Yield: 49%. Rf═0.36 (95/5 v/v CH2Cl2/MeOH).

Workup

  1. temperatureThe solution is refluxed for 4 hours
  2. washafter which the solution is washed twice with water, once with saturated NaHCO3 solution
  3. customwith water until a neutral pH is obtained
  4. customAfter drying
  5. filtrationthe organic phase (MgSO4), filtration
  6. customon paper and evaporation of the solvents
  7. customthe residue is chromatographed on a column of silica gel
  8. washeluting with an MeOH/CH2Cl2 mixture (0.5/99.5 v/v)

Sources & evidence

ORD record
ord-b8714528d34e4dab8255c35074052a3c
Source dataset
uspto-grants-2003_03
Patent number
US06531476B1

Reaction notes

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