Triethylamine → HCID 66751340, compound

HRID 534978Notes

Reaction equation

HRID 534978 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:29])[C:20]([NH:22][CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[O:21])[CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].Cl[C:31](=[O:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>O1CCCC1>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:14][CH2:15][N:16]([C:19](=[O:29])[C:20]([NH:22][CH:23]2[CH2:24][CH2:25][N:26]([C:31](=[O:37])[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:27][CH2:28]2)=[O:21])[CH2:17][CH2:18]1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 20884Ethoxalyl chlorideHCID 516892Sodium BicarbonateHCID 66751186HCID 66751186, compound

Product 1

HCID 66751340HCID 66751340, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-[4-(2 tert-butylphenyl)piperazin-1-yl]-2-oxo-N-piperidin-4-ylacetamide dihydrochloride (Example 182-A, 0.35 g, 0.79 mmol), ethyl chloro(oxo)acetate (140 mg, 1.02 mmol) and triethylamine (439 3.15 mmol) in tetrahydrofuran (4 mL) was stirred at room temperature for 12 days. The reaction mixture was poured into saturated NaHCO3 solution and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate 75:25 to 25:75) to give the title compound (0.33 g, 88%) as a white amorphous.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate 75:25 to 25:75)

Sources & evidence

ORD record
ord-fe7c3d15692a4d2f92da7257377c28ba
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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