1,1-Dibromoethane → 10-[3-(N,N-diethylamino)propyl]-5-methyl-5H-pyrido[3,4-f]pyrrolo-[1,2-b] [1,2,5]triazepine

HRID 982328Notes

Reaction equation

HRID 982328 reaction equation
[Mg].[CH2:2]([N:4]([CH2:9][CH3:10])[CH2:5][CH2:6][CH2:7]Cl)[CH3:3].BrC(Br)C.[CH3:15][N:16]1[C:22]2[CH:23]=[CH:24][N:25]=[CH:26][C:21]=2[N:20]=[CH:19][C:18]2=[CH:27][CH:28]=[CH:29][N:17]12.[Cl-].[NH4+]>C(OCC)C.O1CCCC1>[CH2:2]([N:4]([CH2:5][CH2:6][CH2:7][C:19]1[C:18]2[N:17]([CH:29]=[CH:28][CH:27]=2)[N:16]([CH3:15])[C:22]2[CH:23]=[CH:24][N:25]=[CH:26][C:21]=2[N:20]=1)[CH2:9][CH3:10])[CH3:3]

Participants

8

Reactant 5

HCID 112011,1-DibromoethaneHCID 25517Ammonium ChlorideHCID 669183-Chloropropyl(diethyl)amineHCID 5462224MagnesiumHCID 146019475-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine

Product 1

HCID 6792859710-[3-(N,N-diethylamino)propyl]-5-methyl-5H-pyrido[3,4-f]pyrrolo-[1,2-b] [1,2,5]triazepine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
70 °C

Procedure

To magnesium turnings (1.9 g) in 10 ml of diethyl ether and 10 ml of tetrahydrofuran, was added a solution of 11.66 g of 3-diethylaminopropyl chloride in 10 ml of tetrahydrofuran. The reaction was initiated by the addition of 1 ml of dibromoethane and the application of heat. After stirring at 70° C. for four hours, the reaction mixture cooled to room temperature and treated, dropwise, with a solution of 7.7 g of 5-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine in 50 ml of tetrahydrofuran. The mixture was then stirred at room temperature for two hours, poured into an iced ammonium chloride solution, and extracted with ethyl acetate (3×). The combined extracts were washed with water followed by a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated. High pressure liquid chromatography of the concentrate (silica gel; elution with 15% methanol/dichloromethane) afforded 10-[3-(N,N-diethylamino)propyl]-5-methyl-5H-pyrido[3,4-f]pyrrolo-[1,2-b] [1,2,5]triazepine as an oil. The oil was dissolved in ethanol and acidified with an ethanol solution of fumaric acid. Diluting with diethyl ether precipitated 3.05 g of the corresponding sesquifumarate salt, mp 170°-172° C.

Workup

  1. temperaturethe application of heat
  2. temperaturethe reaction mixture cooled to room temperature
  3. additiontreated
  4. stirringThe mixture was then stirred at room temperature for two hours
  5. extractionextracted with ethyl acetate (3×)
  6. washThe combined extracts were washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. concentrationHigh pressure liquid chromatography of the concentrate
  11. wash(silica gel; elution with 15% methanol/dichloromethane)

Sources & evidence

ORD record
ord-c6093c7ee53f46799833d313e2aec43f
Source dataset
uspto-grants-1991_02
Patent number
US04996205

Reaction notes

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