Sodium hydride → 11-[3-(N-Ethyl-N-isopropyl-amino)-propyl]-6,11-dihydro-2,6-dimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one

HRID 1862977Notes

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][CH2:28][CH2:29]Cl)[CH:24]([CH3:26])[CH3:25])[CH3:22]>O1CCOCC1>[CH2:21]([N:23]([CH2:27][CH2:28][CH2:29][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)[CH:24]([CH3:26])[CH3:25])[CH3:22]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture consisting of 4.5 gm of 6,11-dihydro-2,6-dimethyl-5H-pyrido-[2,3-b][1,5]benzodiazepin-5-one, 60 ml of dioxane and 1.27 gm of 50% sodium hydride in mineral oil was stirred at 90° C. for 1 hour. Thereafter, 4.3 gm of 3-(N-ethyl-N-isopropyl-amino)-propyl chloride were added dropwise, and the mixture was refluxed for 17 hours. The reaction solution was then evaporated in vacuo, and the residue was purified over a silica gel column and recrystallized from petroleum ether, yielding 36% of theory of the compound named in the heading, which had a melting point of 104°-105° C.

Workup

temperaturethe mixture was refluxed for 17 hours
customThe reaction solution was then evaporated in vacuo
customthe residue was purified over a silica gel column
customrecrystallized from petroleum ether
customyielding 36% of theory of the compound

Sources & evidence

ORD record: ord-bfc210417daa4cdca3cf28387a0e9740
Source dataset: uspto-grants-1979_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04167570

Reaction notes

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