Water → HCID 15586689, compound

HRID 543625Notes

Reaction equation

HRID 543625 reaction equation
[H-].[Na+].[C:3]1([C:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:12]3[N:20]=[CH:21][CH:22]=[CH:23][C:11]=3[N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:25][CH2:26][CH2:27][N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38].O>CN(C)C=O>[O:38]=[C:29]1[C:30]2[C:31](=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:32](=[O:33])[N:28]1[CH2:27][CH2:26][CH2:25][N:13]1[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[N:10][C:11]2[CH:23]=[CH:22][CH:21]=[N:20][C:12]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 135626384HCID 135626384, compound

Product 1

HCID 15586689HCID 15586689, compoundYield 43.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of 0.56 g (0.023 mole) of sodium hydride in 25 ml of anhydrous dimethylformamide was added, portionwise, 5.0 g (0.0184 mole) of 6-phenyl-11H-pyrido[2,3-b][1,4]benzodiazepine. The reaction mixture was warmed to 80°±2° C. for 1 hr and cooled to room temperature. A solution of 5.55 g (0.020 mole) of N-(3-bromopropyl) phthalimide in 10 ml of anhydrous dimethylformamide was added dropwise and after stirring for 16 hr the reaction mixture was poured into 650 ml of water and stirred for 30 min. The yellow solid was collected by filtration and recrystallized three times from isopropyl alcohol to give 3.7 g of product, m.p. 170°-172° C.

Workup

  1. additionwas added
  2. temperatureThe reaction mixture was warmed to 80°±2° C. for 1 hr
  3. stirringstirred for 30 min
  4. filtrationThe yellow solid was collected by filtration
  5. customrecrystallized three times from isopropyl alcohol

Sources & evidence

ORD record
ord-1bc049322eb64a4b95aca4e98b0adbb3
Source dataset
uspto-grants-1984_05
Patent number
US04447361

Reaction notes

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