Sodium hydride → 6,11-Dihydro-11-(3-diisopropylamino-propyl)-2,6-dimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one

HRID 1862978Notes

Reaction equation

HRID 1862978 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=[O:12])[N:10]([CH3:13])[C:9]3[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=3[NH:7][C:6]=2[N:18]=1.[H-].[Na+].[CH:21]([N:24]([CH:29]([CH3:31])[CH3:30])[CH2:25][CH2:26][CH2:27]Cl)([CH3:23])[CH3:22]>CN(C)C=O>[CH:21]([N:24]([CH:29]([CH3:31])[CH3:30])[CH2:25][CH2:26][CH2:27][N:7]1[C:8]2[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=2[N:10]([CH3:13])[C:11](=[O:12])[C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[N:18][C:6]1=2)([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 129354311-Diisopropylamino-3-chloropropaneHCID 203930286,11-Dihydro-2,6-dimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one

Product 1

HCID 203930246,11-Dihydro-11-(3-diisopropylamino-propyl)-2,6-dimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture consisting of 4.5 gm of 6,11-dihyrdo-2,6-dimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, 60 ml of dimethyl formamide and 1.27 gm of 50% sodium hydride in mineral oil was stirred at 90° C. for 1 hour. Thereafter, 4.6 gm of 3-diisopropylamino-propyl chloride were added dropwise and the mixture was stirred at 120° C. for 2 hours. The reaction solution was then evaporated in vacuo, and the residue was dissolved in a mixture of ether and dilute ammonia. The organic phase was separated, dried over sodium sulfate and evaporated. The oily residue was distilled, and the fraction passing over between 189°-193° C. at 0.13 mm Hg was recrystallized from petroleum ether, yielding 31% of theory of the compound named in the heading, which had a melting point of 118°-119° C.

Workup

  1. stirringthe mixture was stirred at 120° C. for 2 hours
  2. customThe reaction solution was then evaporated in vacuo
  3. dissolutionthe residue was dissolved in a mixture of ether and dilute ammonia
  4. customThe organic phase was separated
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. distillationThe oily residue was distilled
  8. custompassing over between 189°-193° C. at 0.13 mm Hg
  9. customwas recrystallized from petroleum ether
  10. customyielding 31% of theory of the compound

Sources & evidence

ORD record
ord-83fe4410a38145b79d37abe0fd26cf99
Source dataset
uspto-grants-1979_09
Patent number
US04167570

Reaction notes

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