Sodium Carbonate → 11-[[[2-[2-[(Diethylamino)methyl]-piperidin-1-yl]ethyl]amino]carbonyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 2351385Notes

Reaction equation

HRID 2351385 reaction equation
Cl[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].C(=O)([O-])[O-].[Na+].[Na+].[CH2:26]([N:28]([CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][N:33]1[CH2:38][CH2:39][NH2:40])[CH2:29][CH3:30])[CH3:27]>C(#N)C>[CH2:26]([N:28]([CH2:31][CH:32]1[CH2:37][CH2:36][CH2:35][CH2:34][N:33]1[CH2:38][CH2:39][NH:40][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])[CH2:29][CH3:30])[CH3:27]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 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 1421002811-[[[2-[2-[(Diethylamino)methyl]-piperidin-1-yl]ethyl]amino]carbonyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.2 g (0.0117 mol) of 11-(chlorocarbonyl)-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one and 1.27 g (0.012 mol) of anhydrous sodium carbonate were heated to 60° C. for 4 hours in 100 ml of dry acetonitrile together with 3.0 g (0.014 mol) of 2-[2-[(diethylamino)-methyl]-piperidin-1-yl]ethanamine with stirring. The mixture was filtered while hot, the filtrate was cooled and the substance which crystallised out was suction filtered. 2.7 g (51% of theory) of colourless cyrstals were obtained, m.p. 175°-176° C.

Workup

  1. filtrationThe mixture was filtered while hot, the filtrate
  2. temperaturewas cooled
  3. customthe substance which crystallised out
  4. filtrationfiltered
  5. custom2.7 g (51% of theory) of colourless cyrstals were obtained

Sources & evidence

ORD record
ord-48fc7e5b71254c71aa5a7c65a7cbbc30
Source dataset
uspto-grants-1989_10
Patent number
US04873236

Reaction notes

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