Triethylamine → HCID 90459747, compound

HRID 588821Notes

Reaction equation

HRID 588821 reaction equation
[C:1]([CH:4]1[NH:9][CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5]1)(=[O:3])[NH2:2].CCN(CC)CC.[C:24](Cl)(=[O:27])[CH:25]=[CH2:26]>C(Cl)Cl>[C:24]([N:9]1[CH2:8][CH2:7][N:6]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:5][CH:4]1[C:1](=[O:3])[NH2:2])(=[O:27])[CH:25]=[CH2:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 11042527Tert-butyl 3-carbamoylpiperazine-1-carboxylate

Product 1

HCID 90459747HCID 90459747, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 3-carbamoylpiperazine-1-carboxylate (300 mg, 1.31 mmol) and Et3N (396 mg, 3.93 mmol) in DCM (5 mL) at 0° C., acryloyl chloride (130 mg, 1.44 mmol) in DCM (1 mL) was added and the resulting mixture was stirred at room temperature for 1.5 h. The mixture was partitioned between DCM and saturated NaHCO3 aqueous solution. The organic layer was washed with saturated NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (DCM/MeOH=30:1) to afford the desired product (200 mg, 53.9% yield) as an off-white solid.

Workup

  1. customThe mixture was partitioned between DCM and saturated NaHCO3 aqueous solution
  2. washThe organic layer was washed with saturated NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel (DCM/MeOH=30:1)

Sources & evidence

ORD record
ord-be20e3244c464f3abb1372a2a69db459
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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