4-Methylmorpholine → 2-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate

HRID 417949

Reaction equation

HRID 417949 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[CH3:14][N:15]1[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][OH:23])[CH2:17][CH2:16]1.CN1CCOCC1>C(Cl)Cl>[C:2](=[O:3])([O:4][C:5]1[CH:6]=[CH:7][C:8]([N+:11]([O-:13])=[O:12])=[CH:9][CH:10]=1)[O:23][CH2:22][CH2:21][N:18]1[CH2:19][CH2:20][N:15]([CH3:14])[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 821294-Nitrophenyl chloroformateHCID 2311841-(2-Hydroxyethyl)-4-methylpiperazine

Product 1

HCID 574450072-(4-Methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonateYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-Nitrophenyl chloroformate (9.85 g, 49 mmol) was dissolved in DCM (200 mL), and cooled to 0° C. 2-(4-methylpiperazin-1-yl)ethanol (7.2 g, 50 mmol) and NMM (6 mL) were added, and the reaction mixture was allowed to warm gradually to room temperature over 16 hours. The reaction mixture was washed with 1M aq Na2CO3 solution until the yellow colour extracted into the aqueous layer had disappeared. The organic phase was dried (MgSO4), filtered and concentrated in vacuo to give 2-(4-methylpiperazin-1-yl)ethyl 4-nitrophenyl carbonate (10.7 g, 71%) as a yellow oil which solidified on standing.

Workup

  1. temperatureto warm gradually to room temperature over 16 hours
  2. washThe reaction mixture was washed with 1M aq Na2CO3 solution until the yellow colour
  3. extractionextracted into the aqueous layer
  4. dry with materialThe organic phase was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8ad9bf268d63479fb27969f8cffcb832
Source dataset
uspto-grants-2012_01
Patent number
US08093248B2

Linked notes

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