Hydrochloric Acid → HCID 22004788, compound

HRID 1636616Notes

Reaction equation

HRID 1636616 reaction equation
[OH:1][C:2]1[C:10]([OH:11])=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[CH2:12][CH2:13][NH:14][C:15](=[O:19])[CH2:16][CH2:17][CH3:18])=[CH:4][CH:3]=1.Br[CH2:21]Br.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O.[Cu]=O.O>[O:11]1[C:10]2[C:9]3[CH:8]([CH2:12][CH2:13][NH:14][C:15](=[O:19])[CH2:16][CH2:17][CH3:18])[CH2:7][CH2:6][C:5]=3[CH:4]=[CH:3][C:2]=2[O:1][CH2:21]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 3024DibromomethaneHCID 11430Potassium CarbonateHCID 22004789HCID 22004789, compound

Product 1

HCID 22004788HCID 22004788, compoundYield 67%

Reagents, catalysts & solvents 3

HCID 14829Copper oxideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of N-[2-(6,7-dihydroxyindan-1-yl)ethyl]butyramide (1.13 g, 4.29 mmol.), dibromomethane (2.98 g, 17.2 mmol.), potassium carbonate (1.78 g, 12.9 mmol.) and copper-(II) oxide (34 mg, 0.43 mmol.) in N,N-dimethylformamide (15 mL) was stirred for 3 hours at 110° C. The reaction mixture was cooled, which was poured into water, followed by neutralizing with dilute hydrochloric acid. The organic matter was extracted with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution and water, which was then dried over anhydrous magnesium sulfate, followed by distilling off the solvent under reduced pressure. The residue was purified by means of silica gel column chromatography (ethyl acetate) to afford the title compound (yield 785 mg, 67%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionThe organic matter was extracted with ethyl acetate
  3. washThe extract solution was washed with a saturated aqueous saline solution and water, which
  4. dry with materialwas then dried over anhydrous magnesium sulfate
  5. distillationby distilling off the solvent under reduced pressure
  6. customThe residue was purified by means of silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-866d5ae17b9e410597402da8c9449403
Source dataset
uspto-grants-2000_03
Patent number
US06034239

Reaction notes

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