11-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one → HCID 19846062, compound

HRID 2351384Notes

Reaction equation

HRID 2351384 reaction equation
[Cl:1][C:2]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[NH:7][C:6]2[CH:16]=[CH:17][CH:18]=[N:19][C:5]1=2)=[O:3].[CH2:20]([N:22]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][N:27]1[CH2:32][CH2:33][NH2:34])[CH2:23][CH3:24])[CH3:21]>C(#N)C>[ClH:1].[CH2:20]([N:22]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][N:27]1[CH2:32][CH2:33][NH:34][C:2]([N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[NH:7][C:6]2[CH:16]=[CH:17][CH:18]=[N:19][C:5]1=2)=[O:3])[CH2:23][CH3:24])[CH3:21]

Participants

4

Reactant 2

HCID 1104396211-chlorocarbonyl-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneHCID 142100002-[2-[(Diethylamino)methyl]piperidin-1-yl]ethanamine

Product 1

HCID 19846062HCID 19846062, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 33.4 g (0.122 mol) of 11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 28.0 g (0.131 mol) of 2-[2-[(diethylamino)methyl]piperidin-1-yl]ethanamine and 730 ml of anhydrous acetonitrile was stirred for 3 hours at a reaction temperature of 45° C. After standing for 1 hour in an ice bath, the precipitate formed was suction filtered and washed with ice cold acetonitrile. It was dissolved in 400 ml of hot ethanol, 4.6 g of activated charcoal were added, the mixture was filtered whilst hot and the filtrate was evaporated down in vacuo. The residue remaining was dissolved in 150 ml of hot propan-2-ol and stirred at a temperature of 75° C. for 2 hours after the careful addition of 800 ml of ethyl acetate. The mixture was then left to stand for 2 hours at ice bath temperature, the crystals produced were suction filtered and thoroughly washed three times with 20 ml aliquots of ethyl acetate. 37.0 g (62% of theory) of colourless crystals were obtained, m.p. 200°-202° C.

Workup

  1. waitAfter standing for 1 hour in an ice bath
  2. customthe precipitate formed
  3. filtrationfiltered
  4. washwashed with ice cold acetonitrile
  5. dissolutionIt was dissolved in 400 ml of hot ethanol
  6. addition4.6 g of activated charcoal were added
  7. filtrationthe mixture was filtered whilst hot and the filtrate
  8. customwas evaporated down in vacuo
  9. dissolutionThe residue remaining was dissolved in 150 ml of hot propan-2-ol
  10. stirringstirred at a temperature of 75° C. for 2 hours
  11. additionafter the careful addition of 800 ml of ethyl acetate
  12. waitThe mixture was then left
  13. waitto stand for 2 hours at ice bath
  14. customtemperature, the crystals produced
  15. filtrationwere suction filtered
  16. washthoroughly washed three times with 20 ml aliquots of ethyl acetate
  17. custom37.0 g (62% of theory) of colourless crystals were obtained

Sources & evidence

ORD record
ord-c88d9c3c0e344e70b98a6ab7dd21bcc5
Source dataset
uspto-grants-1989_10
Patent number
US04873236

Reaction notes

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