Sodium Carbonate → 11-[(1-Ethyl-3-piperidyl)aminoacetyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

HRID 2057387Notes

Reaction equation

HRID 2057387 reaction equation
Cl[CH2:2][C:3]([N:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[NH:8][C:7]2[CH:17]=[CH:18][CH:19]=[N:20][C:6]1=2)=[O:4].C(=O)([O-])[O-].[Na+].[Na+].[CH2:27]([N:29]1[CH2:34][CH2:33][CH2:32][CH:31]([NH2:35])[CH2:30]1)[CH3:28]>C(O)C>[CH2:27]([N:29]1[CH2:34][CH2:33][CH2:32][CH:31]([NH:35][CH2:2][C:3]([N:5]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[C:9](=[O:16])[NH:8][C:7]3[CH:17]=[CH:18][CH:19]=[N:20][C:6]2=3)=[O:4])[CH2:30]1)[CH3:28]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 980943-amino-N-ethylpiperidineHCID 12005311-(Chloroacetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-one

Product 1

HCID 5411380711-[(1-Ethyl-3-piperidyl)aminoacetyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.2 gm of 11-chloroacetyl-5,11-dihydro-6H-pyrido [2,3-b][1,4]benzodiazepin-6-one, 2.8 gm of sodium carbonate and 3.8 gm of 1-ethyl-3-amino-piperidine were refluxed in 100 ml of ethanol for 5 hours. Then the hot mixture was suction-filtered, the filtrate was evaporated in vacuo to dryness, and the residue was purified on a silica gel column. The evaporation residue of the eluate was recrystallized from ethyl acetate.

Workup

  1. filtrationThen the hot mixture was suction-filtered
  2. customthe filtrate was evaporated in vacuo to dryness
  3. customthe residue was purified on a silica gel column
  4. customThe evaporation residue of the eluate was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-80319252dde94672b15a5e9385cbdab7
Source dataset
uspto-grants-1980_07
Patent number
US04210648

Reaction notes

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