Sodium Hydroxide → HCID 86758004, compound

HRID 844212Notes

Reaction equation

HRID 844212 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1.Cl.Cl[CH2:15][CH2:16][NH2:17].[C:18]([OH:25])(=[O:24])/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.CC(O)C.C(#N)C>[C:18]([OH:25])(=[O:24])/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22].[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][N:10]2[CH2:15][CH2:16][NH2:17])=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 444972Fumaric AcidHCID 6764936-BromoindoleHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 86758004HCID 86758004, compoundYield 81.1%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of powdered sodium hydroxide (0.41 g, 10.2 mmol), tetrabutylammonium hydrogensulfate (0.034 g, 0.1 mmol), 6-bromoindole (0.5 g, 2.5 mmol) and acetonitrile (15 mL) was added 2-chloroethylamine hydrochloride (0.31 g, 2.75 mmol). The mixture heated under reflux for 16 h and partitioned between water (30 mL) and ether (2×30 mL). The combined organic extracts were washed with brine (2×), dried (magnesium sulfate), concentrated in vacuo and purified by column chromatography [SiO2; ethyl acetate-methanol-0.880 ammonia solution (90:9:1)] to give a pale brown oil. The oil was dissolved in 2-propanol (10 mL) and the solution was heated to reflux, fumaric acid (0.29 g, 2.5 mmol) was added and the mixture was cooled to room temperature and filtered. The filter-cake was dried in vacuo to give the product (0.72 g, 81% yield) as a white solid: mp 214-216° C.; NMR δH (400 MHz, DMSO-d6) 3.08 (2H, t, J 8 Hz), 4.33(2H, t, J 8 Hz), 6.47-6.52 (1H, m), 7.14-7.19 (1H, m), 7.41-7.44 (1H, m), 7.52 (1H, d, J 6.5 Hz) and 7.82 (1H, brs).

Workup

  1. temperatureThe mixture heated
  2. temperatureunder reflux for 16 h
  3. custompartitioned between water (30 mL) and ether (2×30 mL)
  4. washThe combined organic extracts were washed with brine (2×)
  5. dry with materialdried (magnesium sulfate)
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography [SiO2; ethyl acetate-methanol-0.880 ammonia solution (90:9:1)]
  8. customto give a pale brown oil
  9. temperaturethe solution was heated
  10. temperatureto reflux
  11. filtrationfiltered
  12. customThe filter-cake was dried in vacuo

Sources & evidence

ORD record
ord-68a0aa7f03774e55934a370a336aa802
Source dataset
uspto-grants-2002_04
Patent number
US06380238B1

Reaction notes

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