Hydrochloric Acid → HCID 57308572, compound

HRID 439877Notes

Reaction equation

HRID 439877 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:20]=1[C:9]1[NH:10][C:11]3[C:12]([CH3:19])=[CH:13][C:14]([O:17][CH3:18])=[CH:15][C:16]=3[C:8]=1[CH2:7]2.[B].C1NCCOC1.Cl.[OH-].[Na+]>O.O1CCOCC1>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:20]=1[C@H:9]1[NH:10][C:11]3[C:12]([CH3:19])=[CH:13][C:14]([O:17][CH3:18])=[CH:15][C:16]=3[C@H:8]1[CH2:7]2

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 6327109HCID 6327109, compoundHCID 22408431HCID 22408431, compound

Product 1

HCID 57308572HCID 57308572, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

16 ml dioxane, 1.3 g (4.9 mmol) 5,10-dihydro-4,6-dimethyl-8-methoxyindeno[1,2-b]indole and 1.98 g (19.6 mmol) morpholineborane were added to a round bottom flask. 4 ml hydrochloric acid (conc.) was added dropwise during stirring of the solution. The reaction mixture was refluxed for 1 hour. 8 ml (6M) hydrochloric acid was added and the solution was refluxed for 30 min. After the solution had reached room temperature, 50 ml water was added. The mixture was made basic with NaOH(aq) until pH 9. The product was extracted with dichloromethane two times. The organic phase was dried with Na2SO4 and the solvent was evaporated. The product was subjected to chromatography in dichloromethane. The isolated product was dissolved in acetonitrile, a saturated solution of HCl(g) in ether was added and the product precipitated as the hydrochloride salt and was removed by filtration. 1.2 g (82.2%) of product was isolated. 1H NMR (CDCl3):2.33 (3H,s), 2.48 (3H, s), 2.95 (1H, dd), 3.56 (1H, dd), 3.77 (3H, s), 4.44 (1H, ddd), 5.71 (1H, d), 6.78 (1H, s), 6.93 (1H, s), 7.11-7.17 (2H, m), 7.30 (1H, d).

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. temperaturethe solution was refluxed for 30 min
  3. customhad reached room temperature
  4. extractionThe product was extracted with dichloromethane two times
  5. dry with materialThe organic phase was dried with Na2SO4
  6. customthe solvent was evaporated
  7. dissolutionThe isolated product was dissolved in acetonitrile
  8. additiona saturated solution of HCl(g) in ether was added
  9. customthe product precipitated as the hydrochloride salt
  10. customwas removed by filtration

Sources & evidence

ORD record
ord-96799d4e0f304ebdb62b102e17ad017c
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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