Hydrochloric Acid → HCID 57168471, compound

HRID 439850Notes

Reaction equation

HRID 439850 reaction equation
[CH:1]([C:4]1[C:12]2[NH:11][C:10]3[C:13]4[C:18]([CH2:19][C:9]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1)=[CH:17][CH:16]=[CH:15][CH:14]=4)([CH3:3])[CH3:2].O1CCN(B)CC1.Cl.[OH-].[Na+]>O1CCOCC1>[CH:1]([C:4]1[C:12]2[NH:11][C@@H:10]3[C:13]4[C:18]([CH2:19][C@@H:9]3[C:8]=2[CH:7]=[CH:6][CH:5]=1)=[CH:17][CH:16]=[CH:15][CH:14]=4)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 5028646HCID 5028646, compoundHCID 22408491HCID 22408491, compound

Product 1

HCID 57168471HCID 57168471, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4.95 g (0.020 mol) of 5.10-dihydro-6-isopropylindeno[1,2-b]indole and 8.08 g (0.080 mol) of morpholino borane in 25 ml of dioxane was added dropwise 7 ml of conc. hydrochloric acid. The mixture was refluxed for 30 minutes, cooled to room temperature whereupon 20 ml of 6M hydrochloric acid was added. The mixture was refluxed for 15. After cooling the mixture was alkalinized by addition of aqueous sodium hydroxide and extracted three times with ether. Drying (MgSO4) and evaporation gave a crude product which was purified by column chromatography on silica gel using methylene chloride/light petroleum (20/80) as eluent. Thus 3.53 g (71%) of the title compound was obtained. 1H NMR(CDCl3) δ: 1.19 (3H,d), 1.29 (3H, d), 2.84 (1 h,dq), 3,26 (1H,dd), 3.56 (1H,dd), 4,24 (1H,td), 5.31 (1H,d), 6.79 (1H,dd), 6.97 (1H, d), 7.05-7.09 (1H,m), 7,28-7,21 (3H,m), 7.36-7,40 (1H,m).

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. additionwas added
  3. temperatureThe mixture was refluxed for 15
  4. temperatureAfter cooling the mixture
  5. extractionextracted three times with ether
  6. customDrying
  7. custom(MgSO4) and evaporation
  8. customgave a crude product which
  9. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f235cbd859534dd48067420aade41a19
Source dataset
uspto-grants-1996_05
Patent number
US05516788

Reaction notes

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