Triethylamine → HCID 66585107, compound

HRID 1630017Notes

Reaction equation

HRID 1630017 reaction equation
Cl.[N:2]1([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][CH2:6][NH:5][CH:4]([C:8]([O:10][CH3:11])=[O:9])[CH2:3]1.C(N(CC)CC)C.[CH:26]1([C:29](Cl)=[O:30])[CH2:28][CH2:27]1>ClCCl>[CH:26]1([C:29]([N:5]2[CH2:6][CH2:7][N:2]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3][CH:4]2[C:8]([O:10][CH3:11])=[O:9])=[O:30])[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 450721861253789-77-3

Product 1

HCID 66585107HCID 66585107, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution cooled to 0° C. of 10.0 g (35.6 mmol) of 1-tert-butyl 3-methyl piperazine-1,3-dicarboxylate hydrochloride (CAS 129799-08-2) in 350 ml of dichloromethane are added 11.0 ml (79.1 mmol) of triethylamine and then, over 35 minutes, 3.6 ml (40 mmol) of cyclopropylcarbonyl chloride dissolved in 50 ml of dichloromethane. The medium is stirred from 0° C. to room temperature over 4 hours 30 minutes and is then washed with twice 40 ml of water and dried over sodium sulfate. The solvent is evaporated off under reduced pressure and the residue is chromatographed on a column of 90 g of silica gel, eluting with a mixture of 5 to 50% ethyl acetate in dichloromethane, to give 11.5 g 1-tert-butyl 3-methyl 4-cyclopropanecarbonylpiperazine-1,3-dicarboxylate in the form of a viscous oil.

Workup

  1. washis then washed with twice 40 ml of water
  2. dry with materialdried over sodium sulfate
  3. customThe solvent is evaporated off under reduced pressure
  4. customthe residue is chromatographed on a column of 90 g of silica gel
  5. washeluting with a mixture of 5 to 50% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-5658ae82a0694839be93a022ea560653
Source dataset
uspto-grants-2014_07
Patent number
US08791119B2

Reaction notes

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