Hydrochloric Acid → HCID 53766925, compound

HRID 1417468Notes

Reaction equation

HRID 1417468 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]1[C:19]2[NH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH2:10][CH:9]([C:20]([OH:22])=[O:21])[CH2:8]1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.Cl>CN(C)C=O>[CH2:7]1[C:19]2[NH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]=2[CH2:10][CH:9]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 13491214HCID 13491214, compound

Product 1

HCID 53766925HCID 53766925, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5.53 g of powdered potassium carbonate was added to a solution of 4.34 g of 1,2,3,4-tetrahydrocarbazole-3-carboxylic acid, as obtained in Example 49, in 100 ml of N,N-dimethylformamide. 3.76 g of benzyl bromide were added to the reaction mixture, which was then stirred for 1.5 hours at room temperature, after which the mixture was neutralized by the addition of a 0.5N aqueous solution of hydrochloric acid. The aqueous layer was extracted with ethyl acetate. The organic extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography using 150 g of silica gel with a 4:1 v/v mixture of hexane and ethyl acetate as the eluent, and recrystallized from ethyl acetate and hexane, to yield 6.04 g of the title compound, melting at 104°-105° C.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated by evaporation under reduced pressure
  6. additionwith a 4:1 v/v mixture of hexane and ethyl acetate as the eluent
  7. customrecrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-def6e637f4554cada64f3af559841124
Source dataset
uspto-grants-1999_03
Patent number
US05877199

Reaction notes

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