Hydrochloric Acid → HCID 23335370, compound

HRID 903897Notes

Reaction equation

HRID 903897 reaction equation
[CH3:1][NH2:2].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:9](=O)[C:10]3[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=3[CH:12]=[CH:13][C:4]=12.C(=O)([O-])[O-].[K+].[K+].[BH4-].[Na+].Cl>C1C=CC=CC=1.Cl[Ti](Cl)(Cl)Cl>[CH3:1][NH:2][CH:9]1[C:5]2[C:4](=[N:3][CH:8]=[CH:7][CH:6]=2)[CH:13]=[CH:12][C:11]2[CH:14]=[CH:15][CH:16]=[CH:17][C:10]1=2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 11430Potassium CarbonateHCID 1203582HCID 1203582, compoundHCID 4311764Sodium borohydride

Product 1

HCID 23335370HCID 23335370, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 241BenzeneSolvent2×

Conditions

Temperature
25 °C

Procedure

Methylamine (3.72 g., 0.12 mole) is added to a mechanically stirred mixture of benzo[4,5]cyclohepta[1,2-b]pyridin-5-one (6.0 g., 0.03 mole) in benzene (150 ml.). A solution of TiCl4 (2.1 ml.) in benzene (50 ml.) is added and the mixture is stirred at 25° C. for 18 hours. Anhydrous potassium carbonate is added to the mixture and it is filtered through diatomaceous earth. The filtrate is evaporated to an amber oil (5.47 g.) which is dissolved in acetonitrile (150 ml.). Sodium borohydride (5.47 g., 0.025 mole) is added and the mixture is heated on a steam bath for 11/2 hours. Dilute HCl (3N) is added to the cooled reaction mixture and it is evaporated to dryness under reduced pressure. The residue is dissolved in 3N HCl (150 ml.), extracted with ether and the aqueous filtrate is made alkaline by the addition of 40% NaOH solution. The basic material is extracted into CHCl3 and concentrated to an amber oil (3.96 g.). This oil is converted to a hydrochloride salt by treatment with ethanolic hydrogen chloride for use in Step B.

Workup

  1. filtrationis filtered through diatomaceous earth
  2. customThe filtrate is evaporated to an amber oil (5.47 g.) which
  3. dissolutionis dissolved in acetonitrile (150 ml.)
  4. temperaturethe mixture is heated on a steam bath for 11/2 hours
  5. customis evaporated to dryness under reduced pressure
  6. dissolutionThe residue is dissolved in 3N HCl (150 ml.)
  7. extractionextracted with ether
  8. additionby the addition of 40% NaOH solution
  9. extractionThe basic material is extracted into CHCl3
  10. concentrationconcentrated to an amber oil (3.96 g.)

Sources & evidence

ORD record
ord-44e9e78a048c46f5a1361c11cc3ae6a5
Source dataset
uspto-grants-1980_10
Patent number
US04229455

Reaction notes

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