Sodium hydride → 11(3'-dimethylamino-n-propyl)-6,11-dihydro-6-methyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one

HRID 2397455Notes

Reaction equation

HRID 2397455 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]2[N:13]=[CH:14][CH:15]=[CH:16][C:4]=2[C:3]1=[O:17].[H-].[Na+].[CH3:20][N:21]([CH3:36])[CH2:22][CH2:23][CH2:24]OS(C1C=CC(C)=CC=1)(=O)=O>C1(C)C(C)=CC=CC=1>[CH3:20][N:21]([CH3:36])[CH2:22][CH2:23][CH2:24][N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:2]([CH3:1])[C:3](=[O:17])[C:4]2[CH:16]=[CH:15][CH:14]=[N:13][C:5]1=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 4532455H-Pyrido(2,3-b)(1,5)benzodiazepin-5-one, 6,11-dihydro-6-methyl-HCID 214550723-(Dimethylamino)propyl 4-methylbenzene-1-sulfonate

Product 1

HCID 2143832711(3'-dimethylamino-n-propyl)-6,11-dihydro-6-methyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-oneYield 38.7%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 4.5 gm of 6,11-dihydro-6-methyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, 0.83 gm of 55% sodium hydride in mineral oil, and 100 ml of absolute xylene was refluxed for two hours. Thereafter, 7 gm of p-toluenesulfonic acid 3-dimethylamino-n-propyl ester were added, and the resulting mixture was refluxed for 14 hours more. After cooling, the reaction mixture was suction-filtered, and the filtrate was extracted with dilute acetic acid. From the acidic aqueous phase, the base was precipitated as an oil with concentrated ammonia and taken up in ether. After evaporation of the ether solution, the residue was distilled, yielding 2.4 gm of 11(3'-dimethylamino-n-propyl)-6,11-dihydro-6-methyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, b.p. 180°-183° C. at 0.03 mm Hg, which melted at 98.5°-100° C. after crystallization from cyclohexane and recrystallization from petroleum ether.

Workup

  1. temperaturewas refluxed for two hours
  2. temperaturethe resulting mixture was refluxed for 14 hours more
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was suction-filtered
  5. extractionthe filtrate was extracted with dilute acetic acid
  6. customFrom the acidic aqueous phase, the base was precipitated as an oil with concentrated ammonia
  7. customAfter evaporation of the ether solution
  8. distillationthe residue was distilled

Sources & evidence

ORD record
ord-21a852f009b44699b006280233a995ca
Source dataset
uspto-grants-1977_05
Patent number
US04021557

Reaction notes

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