Acetyl chloride → HCID 22110983, compound

HRID 565628Notes

Reaction equation

HRID 565628 reaction equation
Cl.Cl.[CH3:3][C:4]1([CH2:17][N:18]2[CH2:23][CH2:22][CH:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)[CH2:8][C:7]2[C:9]([CH3:16])=[C:10]([NH2:15])[C:11]([CH3:14])=[C:12]([CH3:13])[C:6]=2[O:5]1.C(=O)([O-])[O-].[Na+].[Na+].[C:36](Cl)(=[O:38])[CH3:37]>O1CCCC1.O>[CH3:3][C:4]1([CH2:17][N:18]2[CH2:19][CH2:20][CH:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:22][CH2:23]2)[CH2:8][C:7]2[C:9]([CH3:16])=[C:10]([NH:15][C:36](=[O:38])[CH3:37])[C:11]([CH3:14])=[C:12]([CH3:13])[C:6]=2[O:5]1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 22111064HCID 22111064, compound

Product 1

HCID 22110983HCID 22110983, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2,3-dihydro-2,4,6,7-tetramethyl-2-[(4-phenyl-1-piperidinyl)methyl]-5-benzofuranamine dihydrochloride (1.3 g) in tetrahydrofuran (10 mL) was added a solution of sodium carbonate (0.95 g) in water (5 mL) with ice-cooling and the mixture was stirred for 5 minutes. Then, 0.26 mL of acetyl chloride was added dropwise and the mixture was stirred at room temperature for 15 minutes. This reaction mixture was diluted with water and extracted with 2 portions of ethyl acetate. The pooled organic layer was washed with water and saturated aqueous NaCl, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate/diisopropyl ether to provide 1.1 g of the title compound. Yield 90%.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 15 minutes
  3. extractionextracted with 2 portions of ethyl acetate
  4. washThe pooled organic layer was washed with water and saturated aqueous NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-188a81474bd7446186e6cfb55df2aae7
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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