Pyridine → 3H-1,5-Benzodiazepine, 2,4-bis(4-methyl-1-piperazinyl)-3-propylidene-

HRID 1782398Notes

Reaction equation

HRID 1782398 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]([CH:26](O)[CH2:27][CH3:28])[C:10]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[N:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH-].[Na+]>O1CCCC1.ClCCl.CO>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[C:9](=[CH:26][CH2:27][CH3:28])[C:10]([N:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)=[N:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:7]1

Participants

9

Reactant 5

HCID 1049PyridineHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 100238171-[2,4-bis (4-methyl-1-piperazinyl)-3H-[1,5]benzodiazepin-3-yl]-1-propanol

Product 1

HCID 102492283H-1,5-Benzodiazepine, 2,4-bis(4-methyl-1-piperazinyl)-3-propylidene-Yield 85.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of 1-[2,4-bis(4-methyl-1-piperazinyl)-3H-[1,5]benzodiazepin-3-yl]-1-propanol (1.195 g, 3 mmol), triethylamine (2.50 ml, 18 mmol) and pyridine (0.024 ml, 0.3 mmol) in tetrahydrofuran (10 ml) under constant flow of argon, at 0° C., a solution of trifluoroacetic anhydride (1.26 ml, 9 mmol) in tetrahydrofuran (5 ml) was added dropwise. The reaction mixture was stirred for another hour at 0° C. Methanol (5 ml) was added. The solution was allowed to warm to 10° C., while strongly agitated NaOH (1 M, 20 ml) was added dropwise. Dichloromethane (30 ml) was added and the phases were separated. The organic phase was dried over anhydrous Na2SO4 and the solvent was evaporated at reduced pressure. The crude product was suspended in isopropyl ether (8 ml) and filtered off. The filtrate was evaporated at reduced pressure to give 0.971 g (84%) of the title compound as a yellow resin. The product obtained was characterized using 1H-NMR spectroscopy and was found to be identical to the product obtained by method A.

Workup

  1. additionwas added dropwise
  2. customthe phases were separated
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. customthe solvent was evaporated at reduced pressure
  5. filtrationfiltered off
  6. customThe filtrate was evaporated at reduced pressure

Sources & evidence

ORD record
ord-543564be2c4b452e9aa1c6dde5f5860e
Source dataset
uspto-grants-2009_03
Patent number
US07498433B2

Reaction notes

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