Diisopropylethylamine → HCID 42635797, compound

HRID 417976Notes

Reaction equation

HRID 417976 reaction equation
[C:1](=[O:22])(OC1C=CC([N+]([O-])=O)=CC=1)[O:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([CH3:11])[CH2:7][CH2:6]1.[CH3:23]CN(C(C)C)C(C)C.C[CH:33]1[CH2:38][N:37]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([CH3:45])[CH:40]=2)[CH2:36][CH2:35][NH:34]1>CN(C=O)C>[CH3:23][CH:38]1[N:37]([C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([CH3:45])[CH:40]=2)[CH2:36][CH2:35][N:34]([C:1]([O:2][CH2:3][CH2:4][N:5]2[CH2:6][CH2:7][N:8]([CH3:11])[CH2:9][CH2:10]2)=[O:22])[CH2:33]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 20099350HCID 20099350, compoundHCID 574450072-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate2×

Product 1

HCID 42635797HCID 42635797, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate (Intermediate 4; 2.56 g, 8.28 mmol) was dissolved in DMF (20 mL). DIPEA (1.40 mL, 8.45 mmol) and 2-Methyl-4-(3-methylphenyl)piperazine (1.50 g, 7.87 mmol) were added and the reaction mixture was stirred at room temperature for 24 hours, and the reaction mixture was then concentrated in vacuo. The resulting residue was dissolved in EtOAc (200 mL) and washed with 1 M aq Na2CO3 solution (6×100 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by reverse phase chromatography (gradient eluting with MeOH in water, with 1% formic acid in each solvent, 0-30%). The resulting residue was dissolved in DCM (50 mL) and stirred with solid K2CO3 for 20 minutes, filtered and concentrated in vacuo, give 2-(4-methylpiperazin-1-yl)ethyl 3-methyl-4-(3-methylphenyl)piperazine-1-carboxylate (1.97 g, 69%) as a pale yellow oil.

Workup

  1. concentrationthe reaction mixture was then concentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in EtOAc (200 mL)
  3. washwashed with 1 M aq Na2CO3 solution (6×100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by reverse phase chromatography (gradient
  7. washeluting with MeOH in water, with 1% formic acid in each solvent, 0-30%)
  8. dissolutionThe resulting residue was dissolved in DCM (50 mL)
  9. stirringstirred with solid K2CO3 for 20 minutes
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f81de825ccf344969ed1818d3fef463c
Source dataset
uspto-grants-2012_01
Patent number
US08093248B2

Reaction notes

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