Triethylamine → HCID 66750875, compound

HRID 534971Notes

Reaction equation

HRID 534971 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([CH3:6])([CH3:5])[CH3:4].C(N(CC)CC)C.Cl[C:28](=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C1COCC1>[C:3]([C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[N:14]1[CH2:19][CH2:18][N:17]([C:28](=[O:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:16][CH2:15]1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 66750915HCID 66750915, compound

Product 1

HCID 66750875HCID 66750875, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 1-(2-tert-butyl-4-chlorophenyl)piperazine dihydrochloride (Reference Example 20, 0.50 g, 1.54 mmol) and triethylamine (0.48 g, 4.77 mmol) in THF (30 mL) was added ethyl chloro(oxo)acetate (0.23 g, 1.69 mmol). The mixture was stirred at room temperature for 1 h, filtered and concentrated under reduced pressure. The resulting residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine, died over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by flash column chromatography (silica gel, 9:1-3:7, hexane/ethyl acetate) to give the title compound (0.49 g) as a colorless solid.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe resulting residue was partitioned between ethyl acetate and water
  4. washThe organic layer was washed with saturated brine
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by flash column chromatography (silica gel, 9:1-3:7, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6d6493baa13c4096a918feb581e11bcc
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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