Methane → HCID 19820515, compound

HRID 1030498Notes

Reaction equation

HRID 1030498 reaction equation
I.CS[C:4]1[NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]=1.[C:12]1([CH:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:19][NH2:20])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[ClH:27].C>CO.[OH-].[Na+].C(Cl)Cl>[ClH:27].[C:21]1([CH:18]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:19][NH:20][C:4]2[NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:11]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

8

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 775752,2-DiphenylethylamineHCID 12345492HCID 12345492, compound

Product 1

HCID 19820515HCID 19820515, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

A flask containing 2-methylthio-1,4,5,6,7,8-hexahydro-1,3-diazocine hydroiodide (3.00 g, 1.05×10-2 mole) and 2,2-diphenylethylamine (2.08 g, 1.05×10-2 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. 1 hour. The resulting yellow glass was dissolved in methanol. The methanol was evaporated leaving a foam which was dissolved in a two phase mixture of 5 molar aqueous NaOH (65 ml) and CH2Cl2 (60 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 foam. The foam was dissolved in methanol (15 ml) and the solution was cooled to 0° C. This solution was then treated with a methanolic solution of HCl. The solution was treated with charcoal which was subsequently removed by filtration through a pad of celite. The filtrate was concentrated on the steam bath and 2-butanone was added periodically until the temperature of the solution reached ca. 80° C. Upon cooling the solution deposited a solid which was collected by filtration. This material was recrystallized two times from methanol/2-butanone affording 2-(2,2-diphenylethylamino)-1,4,5,6,7,8-hexahydro-1,3-diazocine hydrochloride as an off-white solid: 0.80 g (22%), m.p. 195°-197° C.

Workup

  1. customwas immersed in an oil bath
  2. customhad been preheated to ca. 155° C
  3. customThe methanol was evaporated
  4. customleaving a foam which
  5. customwas separated
  6. extractionThe aqueous alkaline layer was extracted with CH2Cl2 (2×)
  7. washwashed with H2O (2×)
  8. washwashed with saturated aqueous NaCl
  9. dry with materialdried over anhydrous Na2SO4
  10. customThe drying agent was removed by filtration
  11. customthe filtrate was evaporated at reduced pressure
  12. customleaving a foam
  13. customwas subsequently removed by filtration through a pad of celite
  14. concentrationThe filtrate was concentrated on the steam bath and 2-butanone
  15. additionwas added periodically until the temperature of the solution
  16. customreached ca. 80° C
  17. temperatureUpon cooling the solution
  18. filtrationwas collected by filtration
  19. customThis material was recrystallized two times from methanol/2-butanone

Sources & evidence

ORD record
ord-5aa25ffa0b264182be5b6f7bb6c30fa1
Source dataset
uspto-grants-1992_04
Patent number
US05106845

Reaction notes

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