Diethyl Ether → HCID 21438330, compound

HRID 2397454Notes

Reaction equation

HRID 2397454 reaction equation
[CH3:1][N:2]1[C:8](=[O:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[NH:5][C:4]2[N:14]=[CH:15][CH:16]=[CH:17][C:3]1=2.[H-].[Na+].[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23]Cl.CCOCC>C1(C)C(C)=CC=CC=1.O>[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][N:5]1[C:6]2[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=2[C:8](=[O:9])[N:2]([CH3:1])[C:3]2[CH:17]=[CH:16][CH:15]=[N:14][C:4]1=2

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 79012-Chloro-N,N-dimethylethylamineHCID 24758Sodium hydrideHCID 12184078HCID 12184078, compound

Product 1

HCID 21438330HCID 21438330, compoundYield 45.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7237O-XyleneSolvent

Procedure

9.0 gm of 5,11-dihydro-5-methyl-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one were dissolved in 200 ml of hot absolute xylene, 2.1 gm of 50% sodium hydride in mineral oil were added to the solution, and the mixture was refluxed for two hours. Then, 5.3 gm of 2-dimethylamino-ethyl chloride were added dropwise, and the resulting mixture was refluxed for 16 hours more. The cooled reaction mixture was taken up with a mixture of ether and water, and the organic phase was separated and extracted with dilute acetic acid. Then, the acidic aqueous extract was made alkaline with concentrated aqueous ammonia, and the precipitated oil was extracted with ether. After evaporation of the ether, the residue was distilled, yielding 5.4 gm of 11-(2-dimethylaminoethyl)-5,11-dihydro-5-methyl-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, b.p. 171°-173° C. at 0.006 mm Hg. After crystallization and recrystallization from petroleum ether, 3.2 gm of the substance, m.p. 109°-110° C., were obtained.

Workup

  1. temperaturethe mixture was refluxed for two hours
  2. temperaturethe resulting mixture was refluxed for 16 hours more
  3. customThe cooled reaction mixture
  4. customthe organic phase was separated
  5. extractionextracted with dilute acetic acid
  6. extractionThen, the acidic aqueous extract
  7. extractionthe precipitated oil was extracted with ether
  8. customAfter evaporation of the ether
  9. distillationthe residue was distilled

Sources & evidence

ORD record
ord-43faf9fffd1144bba3e756d70f070090
Source dataset
uspto-grants-1977_05
Patent number
US04021557

Reaction notes

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