Sodium Carbonate → 5,10-Dihydro-5-{[(1-methyl-4-piperidinyl)amino]carbonyl}-11H-dibenzo[b,e][1,4]diazepin-11-one

HRID 325880Notes

Reaction equation

HRID 325880 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]=[CH:19][C:5]1=2)=[O:3].C(=O)([O-])[O-].[Na+].[Na+].[NH2:26][CH:27]1[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]1>C(#N)C>[CH3:33][N:30]1[CH2:31][CH2:32][CH:27]([NH:26][C:2]([N:4]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[C:8](=[O:15])[NH:7][C:6]3[CH:16]=[CH:17][CH:18]=[CH:19][C:5]2=3)=[O:3])[CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 27375314-Amino-1-methylpiperidineHCID 132767455-chlorocarbonyl-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one

Product 1

HCID 103158765,10-Dihydro-5-{[(1-methyl-4-piperidinyl)amino]carbonyl}-11H-dibenzo[b,e][1,4]diazepin-11-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Amounts of 3.2 gm (0.012 mol) of 5-chlorocarbonyl-5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one and 2.1 gm (0.02 mol) of sodium carbonate were refluxed in 100 ml of acetonitrile together with 2.3 ml (0.02 mol) of 4-amino-1-methyl-piperidine for 15 minutes under stirring. The mixture was filtered while hot, and the filtrate was purified over a silica gel column [eluant: acetonitrile; followed by methylene chloride/ethyl acetate/cyclohexane/methanol/ammonia (175:75:23:23:3)]. The desired fraction was concentrated by evaporation in vacuo, and the residue was recrystallized from 50% aqueous acetonitrile.

Workup

  1. filtrationThe mixture was filtered while hot, and the filtrate
  2. customwas purified over a silica gel column [eluant: acetonitrile; followed by methylene chloride/ethyl acetate/cyclohexane/methanol/ammonia (175:75:23:23:3)]
  3. concentrationThe desired fraction was concentrated by evaporation in vacuo
  4. customthe residue was recrystallized from 50% aqueous acetonitrile

Sources & evidence

ORD record
ord-0df0d4fec67040dd931fc7d57441ff1e
Source dataset
uspto-grants-1984_04
Patent number
US04443452

Reaction notes

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