Sodium hydride → HCID 20393036, compound

HRID 1862980Notes

Reaction equation

HRID 1862980 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH3:19])[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+].[CH2:22]([N:24]([CH2:32][CH2:33][CH2:34]Cl)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH3:23]>CN(C)C=O>[CH2:22]([N:24]([CH2:32][CH2:33][CH2:34][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[C:4]([CH3:19])=[CH:3][C:2]([CH3:1])=[N:18][C:6]1=2)[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH3:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 20393030HCID 20393030, compoundHCID 20487347HCID 20487347, compound

Product 1

HCID 20393036HCID 20393036, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture consisting of 12.3 gm of 6,11-dihydro-2,4,6-trimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, 120 ml of dimethyl formamide and 3.05 gm of 50% sodium hydride in mineral oil was stirred at 60° C. for 2 hours. Thereafter, 17 gm of 3-(N-ethyl-N-benzyl-amino)-propyl chloride were added dropwise, and the solution was stirred at 120° C. for 2 hours. After evaporating the solution in vacuo, the residue was distilled, yielding 68% of theory of 11-[3-(N-ethyl-N-benzyl-amino)-propyl]-6,11-dihydro-2,4,6-trimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one having a b.p. of 236°-238° C. at 0.3 mm Hg.

Workup

  1. stirringthe solution was stirred at 120° C. for 2 hours
  2. customAfter evaporating the solution in vacuo
  3. distillationthe residue was distilled

Sources & evidence

ORD record
ord-bced3e7e80094562b37006932fa7340b
Source dataset
uspto-grants-1979_09
Patent number
US04167570

Reaction notes

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