Butyl iodide → HCID 19773340, compound

HRID 1614258Notes

Reaction equation

HRID 1614258 reaction equation
[ClH:1].[C:2]([NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH:10]([NH:16][CH2:17][CH2:18][CH3:19])[CH2:11]2)(=[O:4])[CH3:3].[CH2:20](I)[CH2:21][CH2:22][CH3:23].C(=O)([O-])O.[Na+]>CN(C)C=O.O1CCCC1>[ClH:1].[C:2]([NH:5][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH2:8][CH2:9][CH:10]([N:16]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:17][CH2:18][CH3:19])[CH2:11]2)(=[O:4])[CH3:3]

Participants

6

Reactant 3

HCID 10962Butyl iodideHCID 516892Sodium BicarbonateHCID 19773305HCID 19773305, compound

Product 1

HCID 19773340HCID 19773340, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.83 g (0.010 mol) of 5-acetylamino-2-n-propylamino-tetraline-hydrochloride (Example 4.1.1), 2.76 g (0.015 mol) of n-butyliodide and 1.68 g (0.020 mol) of sodium hydrogen carbonate are refluxed in a mixture of 20 ml of absolute dimethylformamide and 30 ml of absolute tetrahydrofuran for 48 hours with stirring (moment of complete reaction determined by thin layer chromatography). The reaction mixture is concentrated by rotary evaporation, finally at 95° C. under a complete water-jet vacuum. The residue is shaken with 50 ml of methylene chloride and 50 ml of water and the aqueous phase separated is extracted twice more with 15 ml of methylene chloride. The combined extracts are washed with 20 ml of water, dried with sodium sulphate and concentrated by rotary evaporation, finally at 90° C. under a complete water-jet vacuum. The residue is dissolved with 10 ml of ethanol and the solution is acidified with 4.0 ml of 2.5 N ethanolic hydrochloric acid (0.0I mol HCl). After the addition of diethylether until turbidity is just starting, the title compound crystallises. After standing overnight it is suction filtered at 5° C., washed with a mixture of ethanol and ether and dried at 80° C. until a constant weight is obtained. Yield 2.56 g (75.5% of theory), melting point 217° C. After recrystallisation from methanol/ether the melting point does not change.

Workup

  1. custom(moment of complete reaction determined by thin layer chromatography)
  2. concentrationThe reaction mixture is concentrated by rotary evaporation, finally at 95° C. under a complete water-jet vacuum
  3. stirringThe residue is shaken with 50 ml of methylene chloride and 50 ml of water
  4. customthe aqueous phase separated
  5. extractionis extracted twice more with 15 ml of methylene chloride
  6. washThe combined extracts are washed with 20 ml of water
  7. dry with materialdried with sodium sulphate
  8. concentrationconcentrated by rotary evaporation, finally at 90° C. under a complete water-jet vacuum
  9. dissolutionThe residue is dissolved with 10 ml of ethanol
  10. additionAfter the addition of diethylether until turbidity
  11. customthe title compound crystallises
  12. filtrationfiltered at 5° C.
  13. washwashed with a mixture of ethanol and ether
  14. customdried at 80° C. until a constant weight
  15. customis obtained
  16. customAfter recrystallisation from methanol/ether the melting point

Sources & evidence

ORD record
ord-b93eec9e567a4b57b45cd7bea262a9f3
Source dataset
uspto-grants-1993_03
Patent number
US05196454

Reaction notes

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