Hydrochloric Acid → HCID 12993016, compound

HRID 2415389Notes

Reaction equation

HRID 2415389 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[C:22]4[NH:21][C:20]5[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=5)[C:14]=4[CH2:13][CH2:12][N:11]3[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1.[O-][O-].[K+].[K+].C1OCCOCCOCCOCCOCC[O:36]C1.Cl>O.CCOC(C)=O.CN(C=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[C:22]4[NH:21][C:20]5[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=5[C:14](=[O:36])[C:13]=4[CH2:12][N:11]3[CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 28202Dipotassium peroxideHCID 2855718-Crown-6HCID 22640315HCID 22640315, compound

Product 1

HCID 12993016HCID 12993016, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(2,3-Dihydro-5-benzofuranyl)-2-benzyl-2,3,4,9-tetrahydro-1H-β-carboline (prepared as in Example 2) (5.25 g, 13.81 mmol), potassium dioxide (3.92 g, 55.24 mmol) and 18-crown-6 (3.65 g, 13.81 mmol) were mixed with DMF (100 mL) in a 200 mL flask. The reaction mixture was maintained at room temperature overnight. The reaction mixture was slowly added into a separate 500 mL flask containing a mixture of EtOAc (172 mL), H2O (172 mL) and 1N aqueous HCl (50 mL). The mixture was observed to produce tiny gas bubbles. The reaction mixture was stirred at 0° C. for 30 min, resulting in the formation of a precipitate at the surface of the two liquid layers. The precipitate was collected by filtration, washed with H2O (20 mL) and then dried in a vacuum oven to yield the product as a off-white solid.

Workup

  1. additionThe reaction mixture was slowly added into a separate 500 mL flask
  2. additioncontaining
  3. customto produce tiny gas bubbles
  4. customresulting in the formation of a precipitate at the surface of the two liquid layers
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with H2O (20 mL)
  7. customdried in a vacuum oven

Sources & evidence

ORD record
ord-3b214127643e4f409f289d6914706a8d
Source dataset
uspto-grants-2004_11
Patent number
US06818646B2

Reaction notes

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