Triethylamine → HCID 42635793, compound

HRID 417973Notes

Reaction equation

HRID 417973 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.CCN(CC)CC.[CH3:30][C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][C:32]=1[N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1>CN(C=O)C>[NH3:5].[CH3:30][C:31]1[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][C:32]=1[N:38]1[CH2:39][CH2:40][N:41]([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])[CH2:42][CH2:43]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 705421-(2,5-Xylyl)piperazineHCID 574450072-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate2×

Product 2

HCID 222AmmoniaHCID 42635793HCID 42635793, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate (Intermediate 4; 866 mg, 2.8 mmol) was dissolved in DMF (25 mL). NEt3 (0.5 mL, 3.6 mmol) and 4-(2,5-dimethyl-phenyl)piperazine (580 mg, 3.1 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 (50 mL) and washed with 1M aq Na2CO3 solution (5×50 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by normal phase column chromatography (eluting with DCM, followed by a 200:8:1 mixture of DCM:EtOH:NH3) to give 2-(4-methylpiperazin-1-yl)ethyl 4-(2,5-dimethyl-phenyl)piperazine-1-carboxylate (274 mg, 27%) as a yellow oil.

Workup

  1. concentrationthe reaction mixture was then concentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in EtOAc (50 mL)
  3. washwashed with 1M aq Na2CO3 solution (5×50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by normal phase column chromatography (
  7. washeluting with DCM
  8. additionfollowed by a 200:8:1 mixture of DCM

Sources & evidence

ORD record
ord-eb981d6429644a3381b83f69fdadd97b
Source dataset
uspto-grants-2012_01
Patent number
US08093248B2

Reaction notes

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