Diisopropylethylamine → HCID 66650868, compound

HRID 417974Notes

Reaction equation

HRID 417974 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(C(C)C)C(C)C.[Cl:32][C:33]1[CH:34]=[C:35]([N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)[CH:36]=[CH:37][C:38]=1[Cl:39]>CN(C=O)C>[ClH:32].[ClH:32].[ClH:32].[Cl:32][C:33]1[CH:34]=[C:35]([N:40]2[CH2:45][CH2:44][N:43]([C:1]([O:2][CH2:3][CH2:4][N:5]3[CH2:6][CH2:7][N:8]([CH3:11])[CH2:9][CH2:10]3)=[O:22])[CH2:42][CH2:41]2)[CH:36]=[CH:37][C:38]=1[Cl:39]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 936011-(3,4-Dichlorophenyl)piperazineHCID 574450072-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate2×

Product 1

HCID 66650868HCID 66650868, compoundYield 64.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate (Intermediate 4; 680 mg, 2.2 mmol) was dissolved in DMF (20 mL). DIPEA (0.76 mL, 4.4 mmol) and 4-(3,4-dichlorophenyl)piperazine (508 mg, 2.2 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 residue was purified by normal phase column chromatography (eluting with DCM, followed by a 400:8:1 mixture of DCM:EtOH:NH3, followed by a 200:8:1 mixture of DCM:EtOH:NH3) followed by reverse phase column chromatography (gradient eluting with MeOH in water, with 1% formic acid in each solvent, 0-100%). The residue was dissolved in DCM (10 mL) and 2M HCl in Et2O (3 mL) was added. The reaction mixture was then concentrated in vacuo to give 2-(4-methylpiperazin-1-yl)ethyl 4-(3,4-dichlorophenyl)piperazine-1-carboxylate trihydrochloride (182 mg, 17%) as a white solid.

Workup

  1. concentrationthe reaction mixture was then concentrated in vacuo
  2. customThe residue was purified by normal phase column chromatography (
  3. washeluting with DCM
  4. additionfollowed by a 400:8:1 mixture of DCM
  5. additionEtOH:NH3, followed by a 200:8:1 mixture of DCM
  6. washeluting with MeOH in water, with 1% formic acid in each solvent, 0-100%)
  7. dissolutionThe residue was dissolved in DCM (10 mL)
  8. addition2M HCl in Et2O (3 mL) was added
  9. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-990a3279e35844bd98ea42ffcd50de52
Source dataset
uspto-grants-2012_01
Patent number
US08093248B2

Reaction notes

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