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

HRID 1862976Notes

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]([CH2:28]C)[CH2:24][CH2:25][CH2:26]Cl)C>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]([CH2:26][CH2:25][CH2:24][N:23]([CH3:28])[CH3:21])[C:6]=2[N:18]=1

Participants

Conditions

Temperature: 120 °C

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°-50° C. in a nitrogen atmosphere for 30 minutes. Then, a solution of 6.1 gm of 3-diethylamino-propyl chloride in 30 ml of dimethyl formamide was added dropwise, and the mixture was heated on an oil bath at 120° C. for 3 hours and then evaporated in vacuo. The residue was mixed with an aqueous potassium carbonate solution, and the mixture was extracted with ether. The ethereal phase was dried with sodium sulfate and evaporated, and the residue was recrystallized from petroleum ether (b.p. 100°-140° C.), yielding 76% of theory of the compound named in the heading, which had a melting point of 130°-131° C.

Workup

customevaporated in vacuo
additionThe residue was mixed with an aqueous potassium carbonate solution
extractionthe mixture was extracted with ether
dry with materialThe ethereal phase was dried with sodium sulfate
customevaporated
customthe residue was recrystallized from petroleum ether (b.p. 100°-140° C.)
customyielding 76% of theory of the compound

Sources & evidence

ORD record: ord-fbe1de0b0dea4a48925d96834c981e64
Source dataset: uspto-grants-1979_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04167570

Reaction notes

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