Hydrochloric Acid → HCID 19820478, compound

HRID 1030497Notes

Reaction equation

HRID 1030497 reaction equation
[IH:1].[CH3:2][N:3]1[CH2:8][CH2:7][CH2:6][N:5]=[C:4]1SC.[C:11]1([CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:18][CH2:19][NH2:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl>CO>[IH:1].[C:21]1([CH:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:18][CH2:19][NH:20][C:4]2[N:3]([CH3:2])[CH2:8][CH2:7][CH2:6][N:5]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 796983,3-DiphenylpropylamineHCID 12397474HCID 12397474, compound

Product 1

HCID 19820478HCID 19820478, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A flask containing 1-methyl-2-methylthio-1,4,5,6-tetrahydropyrimidine hydroiodide (6.00 g, 2.20×10-2 mole) and 3,3-diphenylpropylamine (4.91 g, 2.32×10-2 mole) was immersed in an oil bath which had been preheated to ca. 155° C. The reaction was stirred at between 150°-165° C. for 50 minutes. The resulting yellow glass was dissolved in methanol. The methanol was partially evaporated at reduced pressure and isopropanol was added. The evaporation was continued being stopped periodically for the addition of small portions of isopropanol. A solid formed which was subsequently collected by filtration. This material was dissolved in a two phase mixture of 5 molar aqueous NaOH (100 ml) and CH2Cl2 (100 ml). After stirring overnight, the CH2Cl2 layer was separated. The aqueous alkaline layer was extracted with CH2Cl2 (2×). The CH2Cl2 layers were combined, washed with H2O (2×), washed with saturated aqueous NaCl, and dried over anhydrous Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure leaving a colorless foam which was dissolved in methanol (50 ml). The solution was cooled to 0° C. before being treated with a methanolic solution of HCl. The methanol was partially evaporated at reduced pressure. 2-Butanone was added and the evaporation was continued on the steam bath until the temperature of the solution reached 78°-79° C. After cooling to room temperature, the solution deposited a solid which was collected by filtration. The product was recrystallized from methanol/2-butanone affording 2-(3,3-diphenyl-propylamino)-1-methyl-1,4,5,6-tetrahydropyrimidine hydroiodide as a colorless solid: 3.44 g (45%), m.p. 178°-180° C.

Workup

  1. customwas immersed in an oil bath
  2. customhad been preheated to ca. 155° C
  3. customThe methanol was partially evaporated at reduced pressure and isopropanol
  4. additionwas added
  5. customThe evaporation
  6. additionwas continued being stopped periodically for the addition of small portions of isopropanol
  7. customA solid formed which
  8. filtrationwas subsequently collected by filtration
  9. dissolutionThis material was dissolved in a two phase mixture of 5 molar aqueous NaOH (100 ml) and CH2Cl2 (100 ml)
  10. stirringAfter stirring overnight
  11. customthe CH2Cl2 layer was separated
  12. extractionThe aqueous alkaline layer was extracted with CH2Cl2 (2×)
  13. washwashed with H2O (2×)
  14. washwashed with saturated aqueous NaCl
  15. dry with materialdried over anhydrous Na2SO4
  16. customThe drying agent was removed by filtration
  17. customthe filtrate was evaporated at reduced pressure
  18. customleaving a colorless foam which
  19. customThe methanol was partially evaporated at reduced pressure
  20. addition2-Butanone was added
  21. customthe evaporation
  22. customreached 78°-79° C
  23. temperatureAfter cooling to room temperature
  24. filtrationwas collected by filtration
  25. customThe product was recrystallized from methanol/2-butanone

Sources & evidence

ORD record
ord-e35e6019d15f47e2a034bd0f63021b5d
Source dataset
uspto-grants-1992_04
Patent number
US05106845

Reaction notes

Loading…