Potassium Carbonate → HCID 21500381, compound

HRID 1729709Notes

Reaction equation

HRID 1729709 reaction equation
C[Mg]Br.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:14]2[CH:22]3[C:17]([CH2:18][CH2:19][CH2:20][CH2:21]3)=[N+:16]([O-:23])[CH2:15]2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13].[C:24](=O)([O-])[O-].[K+].[K+]>CCOCC.O1CCCC1>[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:14]2[CH:22]3[C:17]([CH3:24])([CH2:18][CH2:19][CH2:20][CH2:21]3)[N:16]([OH:23])[CH2:15]2)[CH:9]=[CH:10][C:11]=1[O:12][CH3:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 215003863-(3,4-Dimethoxyphenyl)-1-oxo-3,3a,4,5,6,7-hexahydro-2H-1lambda~5~-indoleHCID 178418573HCID 178418573, compound

Product 1

HCID 21500381HCID 21500381, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A volume of 10 ml of 3M methyl magnesium bromide in ether was added over a period of two minutes to a stirred solution of 4.12 g (0.015 mole) of 3,3a,4,5,6,7-hexahydro-3-(3,4-dimethoxyphenyl)-2H-indole 1-oxide in 25 ml of tetrahydrofuran. The warm solution was stirred for 1/2 hour at room temperature and then added cautiously to 50 ml of ice water. The mixture was stirred for 5 minutes and solid potassium carbonate was added to saturate. The mixture was extracted into 200 ml of ether and the extract was decanted, dried over K2CO3, filtered and concentrated to ca 50 ml volume. The separated crystals were filtered and washed with ether; wt. 2.5 g, mp 147°-149° C. A second crop weighing 0.6 g was obtained for a total weight of 3.1 g (71% yield). The product was recrystallized from ethyl acetate to give pure white crystals melting at 147°-149° C.

Workup

  1. stirringThe mixture was stirred for 5 minutes
  2. concentrationto saturate
  3. extractionThe mixture was extracted into 200 ml of ether
  4. customthe extract was decanted
  5. dry with materialdried over K2CO3
  6. filtrationfiltered
  7. concentrationconcentrated to ca 50 ml volume
  8. filtrationThe separated crystals were filtered
  9. washwashed with ether
  10. customwas obtained for a total weight of 3.1 g (71% yield)
  11. customThe product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-7db36d9d82ee4361a828cdf559135674
Source dataset
uspto-grants-1976_11
Patent number
US03989714

Reaction notes

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