Ethyl chloroformate → HCID 14090597, compound

HRID 556393Notes

Reaction equation

HRID 556393 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.Cl[C:9]([O:11][CH2:12][CH3:13])=[O:10]>CO.O.CC(O)=O>[CH2:12]([O:11][C:9]([N:6]1[CH2:5][CH2:4][NH:3][CH:2]([CH3:1])[CH2:7]1)=[O:10])[CH3:13]

Participants

6

Reactant 2

HCID 10928Ethyl chloroformateHCID 660572-Methylpiperazine

Product 1

HCID 14090597HCID 14090597, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of 2-methylpiperazine (10.0 g) in MeOH (120 mL), H2O (40 mL) and AcOH was added at −5° C. dropwise during 25 min ethyl chloroformate (10 mL) and the reaction mixture was stirred overnight at RT. Then, H2O (100 mL) was added and the MeOH evaporated in vacuo. The aq. phase was diluted with toluene (70 mL), the layers were separated and the org. layer was washed with water (50 mL). The aq. phase was then basified with NaOH (2M, 80 mL) and extracted with toluene (100 mL). The combined org. phases were washed with brine (50 mL), dried over MgSO4 and evaporated in vacuo to give the desired compound (8.5 g).

Workup

  1. customthe MeOH evaporated in vacuo
  2. additionThe aq. phase was diluted with toluene (70 mL)
  3. customthe layers were separated
  4. washlayer was washed with water (50 mL)
  5. extractionextracted with toluene (100 mL)
  6. washphases were washed with brine (50 mL)
  7. dry with materialdried over MgSO4
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-249eee97194443f0aff918117953615c
Source dataset
uspto-grants-2011_11
Patent number
US08058263B2

Reaction notes

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