1,1-Dibromoethane → 10,11-dihydro-5-methyl-10-[3-(N,N-dimethylamino)propyl]-5H-pyrido-[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine

HRID 1638383Notes

Reaction equation

HRID 1638383 reaction equation
[Mg].[CH3:2][N:3]([CH2:5][CH2:6][CH2:7]Cl)[CH3:4].BrC(Br)C.[CH3:13][N:14]1[C:20]2[CH:21]=[CH:22][N:23]=[CH:24][C:19]=2[N:18]=[CH:17][C:16]2=[CH:25][CH:26]=[CH:27][N:15]12.[Cl-].[NH4+]>O1CCCC1>[CH3:13][N:14]1[C:20]2[CH:21]=[CH:22][N:23]=[CH:24][C:19]=2[NH:18][CH:17]([CH2:7][CH2:6][CH2:5][N:3]([CH3:4])[CH3:2])[C:16]2=[CH:25][CH:26]=[CH:27][N:15]12

Participants

7

Reactant 5

HCID 112011,1-DibromoethaneHCID 25517Ammonium ChlorideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 5462224MagnesiumHCID 146019475-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine

Product 1

HCID 1460195210,11-dihydro-5-methyl-10-[3-(N,N-dimethylamino)propyl]-5H-pyrido-[3,4-f]pyrrolo[1,2-b][1,2,5]triazepineYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
70 °C

Procedure

To magnesium turnings (1.4 g) in 10 ml of diether ether and 10 ml of tetrahydrofuran, was added a solution of 6.2 g of 3-(N,N-dimethylamino)propyl chloride in 10 ml of tetrahydrofuran. Initiation of the reaction was achieved by the addition of 1 ml of dibromoethane and the application of heat. After stirring at 70° C. for one hour, the reaction mixture was treated with a solution of 5.0 g of 5-methyl-5H-pyrido[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine in 50 ml of tetrahydrofuran over a period of ten minutes. The reaction mixture was then stirred at 60° C. for thirty minutes, poured into 20 ml of an ammonium chloride solution (iced), stirred for five minutes, and extracted with ethyl acetate. The organic layer was washed with water followed by a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrate was purified by means of high pressure liquid chromatography (silica gel; elution with 50% methanol/dichloromethane) to afford 3.6 g (50%) of 10,11-dihydro-5-methyl-10-[3-(N,N-dimethylamino)propyl]-5H-pyrido-[3,4-f]pyrrolo[1,2-b][1,2,5]triazepine as an oil.

Workup

  1. temperaturethe application of heat
  2. stirringThe reaction mixture was then stirred at 60° C. for thirty minutes
  3. stirringstirred for five minutes
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe concentrate was purified by means of high pressure liquid chromatography (silica gel; elution with 50% methanol/dichloromethane)

Sources & evidence

ORD record
ord-b00ff2c29f074edab29f09603d4d9065
Source dataset
uspto-grants-1989_11
Patent number
US04879382

Reaction notes

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