Diethylaminoethyl chloride → 11-(2-Diethylamino-ethyl)-6,11-dihydro-2,6-dimethyl-5H-pyrido-[2,3-b][1,5]benzodiazepin-5-one

HRID 1862975Notes

Reaction equation

HRID 1862975 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+].[CH2:21]([N:23]([CH2:27][CH3:28])[CH2:24][CH2:25]Cl)[CH3:22]>CN(C)C=O>[CH2:21]([N:23]([CH2:27][CH3:28])[CH2:24][CH2:25][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)[CH3:22]

Participants

5

Reactant 3

HCID 13364Diethylaminoethyl chlorideHCID 24758Sodium hydrideHCID 203930286,11-Dihydro-2,6-dimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one

Product 1

HCID 2039303511-(2-Diethylamino-ethyl)-6,11-dihydro-2,6-dimethyl-5H-pyrido-[2,3-b][1,5]benzodiazepin-5-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

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, 70 ml of dimethyl formamide and 1.9 gm of 50% sodium hydride in mineral oil was stirred at 30° to 50° C. in a nitrogen atmosphere for 30 minutes. Thereafter, a solution of 6.8 gm of 2-diethylaminoethyl chloride in 30 ml of dimethyl formamide was added dropwise, and the mixture was stirred at 100° C. for 2 hours and then evaporated in vacuo. The residue was admixed with an aqueous potassium carbonate solution, and the mixture was extracted with ether. The evaporation residue of the combined ether extracts, which were dried with sodium sulfate, was purified in a silica gel column and recrystallized from petroleum ether (b.p. 100°-140° C.), yielding 62% of theory of the compound of the formula ##STR13## which had a melting point of 91°-93° C.

Workup

  1. stirringthe mixture was stirred at 100° C. for 2 hours
  2. customevaporated in vacuo
  3. extractionthe mixture was extracted with ether
  4. dry with materialThe evaporation residue of the combined ether extracts, which were dried with sodium sulfate
  5. customwas purified in a silica gel column
  6. customrecrystallized from petroleum ether (b.p. 100°-140° C.)
  7. customyielding 62% of theory of the compound of the formula ##STR13## which

Sources & evidence

ORD record
ord-57eac5e2c168471b893a9c8d0392a94a
Source dataset
uspto-grants-1979_09
Patent number
US04167570

Reaction notes

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