Hydrochloric Acid → HCID 19820486, compound

HRID 1030502Notes

Reaction equation

HRID 1030502 reaction equation
I.CS[N:4]1[CH2:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[CH2:7][N:6]=[CH:5]1.[C:15]1([CH:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:22][NH2:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(C)C.[ClH:34]>CO>[ClH:34].[C:24]1([CH:21]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:22][NH:23][C:5]2[NH:4][CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH2:7][N:6]=2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 775752,2-DiphenylethylamineHCID 19820492HCID 19820492, compound

Product 1

HCID 19820486HCID 19820486, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A flask containing 2-methylthio-2,5-dihydro-1H-2,4-benzodiazepine hydroiodide (3.20 g 1.00×10-2 mole) and 2,2-diphenylethylamine (5.91 g, 3.00×10-2 mole) was immersed in an oil bath which had been preheated to ca. 155° C. The reaction was stirred at between 150°-160° C. for ca. 30 minutes. The resulting solid mass was treated with isopropanol and that which did not dissolve was collected by filtration. This guanidine hydroiodide was dissolved in a two phase mixture of 5 molar aqueous NaOH (80 ml) and CH2Cl2 (80 ml). After stirring overnight the CH2Cl2 layer was separated. The aqueous alkaline phase 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 foam which was dissolved in methanol (35 ml). The solution was cooled to 0° C. before being treated with a methanolic solution of HCl. The solution was concentrated to ca. 10-15 ml at which point crystallization began. After standing ca. 30 minutes, isopropanol was added and the flask was refrigerated. After 1-1.5 hour the product was collected by filtration. Recrystallization from methanol/isopropanol afforded 3-(2,2-diphenylethylamino)-2,5-dihydro-1H-2,4-benzodiazepine hydrochloride as colorless crystals: 2.53 g (67%), m.p. 243°-245° C.

Workup

  1. customwas immersed in an oil bath
  2. customhad been preheated to ca. 155° C
  3. dissolutiondid not dissolve
  4. filtrationwas collected by filtration
  5. dissolutionThis guanidine hydroiodide was dissolved in a two phase mixture of 5 molar aqueous NaOH (80 ml) and CH2Cl2 (80 ml)
  6. stirringAfter stirring overnight the CH2Cl2 layer
  7. customwas separated
  8. extractionThe aqueous alkaline phase was extracted with CH2Cl2 (2×)
  9. washwashed with H2O (2×)
  10. washwashed with saturated aqueous NaCl
  11. dry with materialdried over anhydrous Na2SO4
  12. customThe drying agent was removed by filtration
  13. customthe filtrate was evaporated at reduced pressure
  14. customleaving a foam which
  15. concentrationThe solution was concentrated to ca. 10-15 ml at which point crystallization
  16. waitAfter standing ca. 30 minutes
  17. additionisopropanol was added
  18. filtrationAfter 1-1.5 hour the product was collected by filtration
  19. customRecrystallization from methanol/isopropanol

Sources & evidence

ORD record
ord-622329e04644430096add1f133121d59
Source dataset
uspto-grants-1992_04
Patent number
US05106845

Reaction notes

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