Sodium hydride → 6,11-Dihydro-2,6-dimethyl-11-(3-pyrrolidino-propyl)-5H-pyrido[2,3-b][1,5]benzodiazepin5-one

HRID 1862979Notes

Reaction equation

HRID 1862979 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+].[N:21]1([CH2:26][CH2:27][CH2:28]Cl)[CH2:25][CH2:24][CH2:23][CH2:22]1>CN(C)C=O>[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[N:7]([CH2:28][CH2:27][CH2:26][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)[C:6]=2[N:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 113210281-(3-Chloropropyl)-pyrrolidineHCID 203930286,11-Dihydro-2,6-dimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one

Product 1

HCID 203930466,11-Dihydro-2,6-dimethyl-11-(3-pyrrolidino-propyl)-5H-pyrido[2,3-b][1,5]benzodiazepin5-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture consisting of 7.2 gm of 6,11-dihydro-2,6-dimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, 1.9 gm of 50% sodium hydride in mineral oil and 100 ml of dimethyl formamide was stirred at 60°-70° C. for 45 minutes. Thereafter, the mixture was cooled to room temperature, 7.4 gm of 3-pyrrolidino-propyl chloride were added dropwise and the mixture was refluxed for 3 hours. The solvent was then distilled off in vacuo, and the residue was recrystallized twice from acetonitrile, yielding 46% of theory of the compound named in the heading, which had a melting point of 134°-136° C.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. distillationThe solvent was then distilled off in vacuo
  3. customthe residue was recrystallized twice from acetonitrile
  4. customyielding 46% of theory of the compound

Sources & evidence

ORD record
ord-a522f4b935004ff7bf2f124b2296fcfa
Source dataset
uspto-grants-1979_09
Patent number
US04167570

Reaction notes

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