Acetyl chloride → HCID 66792825, compound

HRID 534977Notes

Reaction equation

HRID 534977 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].[C:30](Cl)(=[O:32])[CH3:31].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>O1CCCC1>[C:30]([N:26]1[CH2:25][CH2:24][CH:23]([NH:22][C:20](=[O:21])[C:19]([N:16]2[CH2:15][CH2:14][N:13]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[C:3]([CH3:6])([CH3:4])[CH3:5])[CH2:18][CH2:17]2)=[O:29])[CH2:28][CH2:27]1)(=[O:32])[CH3:31]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 66751186HCID 66751186, compound

Product 1

HCID 66792825HCID 66792825, compoundYield 103.8%

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), acetyl chloride (72.5 mg, 1.02 mmol) and triethylamine (439 μL, 3.15 mmol) in tetrahydrofuran (4 mL) was stirred at room temperature for 16 h. 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 to give The title compound (0.34 g, quant.) as a white powder.

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

Sources & evidence

ORD record
ord-c7ddb84cf7d94a0c8b4b0145d80705b7
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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