Sodium Carbonate → 6H-Pyrido(2,3-b)(1,4)benzodiazepin-6-one, 5,11-dihydro-11-(1-oxo-4-(1-pyrrolidinyl)butyl)-

HRID 2057386Notes

Reaction equation

HRID 2057386 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[C:11](=[O:18])[NH:10][C:9]2[CH:19]=[CH:20][CH:21]=[N:22][C:8]1=2)=[O:6].[NH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O1CCOCC1>[N:23]1([CH2:2][CH2:3][CH2:4][C:5]([N:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:11](=[O:18])[NH:10][C:9]3[CH:19]=[CH:20][CH:21]=[N:22][C:8]2=3)=[O:6])[CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 31268PyrrolidineHCID 1592561711-(4-chlorobutyryl)-5,11-dihydro-6H-pyrido [2,3-b][1,4]-benzodiazepin-6-one

Product 1

HCID 30531036H-Pyrido(2,3-b)(1,4)benzodiazepin-6-one, 5,11-dihydro-11-(1-oxo-4-(1-pyrrolidinyl)butyl)-

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

5.5 gm of 11-(4-chlorobutyryl)-5,11-dihydro-6H-pyrido [2,3-b][1,4]-benzodiazepin-6-one, 1.4 gm of pyrrolidine and 2.1 gm of sodium carbonate were refluxed in a mixture of 80 ml of absolute ethanol and 20 ml of absolute dioxane for 10 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 eluate was evaporated in vacuo to dryness, and the residue was recrystallized from acetonitrile.

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 eluate was evaporated in vacuo to dryness
  5. customthe residue was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-d3fc6026159a44e48314c5092f9e2065
Source dataset
uspto-grants-1980_07
Patent number
US04210648

Reaction notes

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