Hydrochloric Acid → HCID 19710192, compound

HRID 725917Notes

Reaction equation

HRID 725917 reaction equation
Br.[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[OH:12])[CH2:8][CH:7]([N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[CH2:6]2.[C:20](=O)([O-])[O-].[K+].[K+].C(Br)CBr.Cl>CN(C)C=O.C(#N)C.O>[CH2:20]1[O:2][C:3]2[CH:4]=[C:5]3[C:9]([CH2:8][CH:7]([N:13]([CH2:17][CH2:18][CH3:19])[CH2:14][CH2:15][CH3:16])[CH2:6]3)=[CH:10][C:11]=2[O:12]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 19710242HCID 19710242, compound

Product 1

HCID 19710192HCID 19710192, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21891449acetonitrile N,N-dimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5,6-Dihydroxy-2-(di-n-propylamino)indan hydrobromide (400 mg, 1.21 mmol) was dissolved in dimethylformamide/acetonitrile (8 mL, 1:1). Potassium carbonate (1.67 g, 12.1 mmol) and 1,2-dibromomethane (0.09 mL, 1.3 mmol) was added and the mixture was heated at 100° C. overnight. Water was added and the reaction mixture concentrated to remove solvents. The resulting mixture was extracted with ethyl acetate (5×75 mL). The combined organic layers were washed with brine, dried, filtered and concentrated to yield an oil. The crude material was chromatographed (200 g silica gel) eluting with methylene chloride/methanol (19:1) to yield an oil. The oil was converted into the HCl salt and recrystallized using methanol/ethyl acetate/ether: mp 168°-269° C.

Workup

  1. concentrationthe reaction mixture concentrated
  2. customto remove solvents
  3. extractionThe resulting mixture was extracted with ethyl acetate (5×75 mL)
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield an oil
  9. customThe crude material was chromatographed (200 g silica gel)
  10. washeluting with methylene chloride/methanol (19:1)
  11. customto yield an oil
  12. customrecrystallized

Sources & evidence

ORD record
ord-b2d5325784844b72b91ec24c023d8053
Source dataset
uspto-grants-1998_01
Patent number
US05708018

Reaction notes

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