Sodium hydride → HCID 20393045, compound

HRID 1862982Notes

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+].[O:22]1[CH2:27][CH2:26][N:25]([CH2:28][CH2:29]Cl)[CH2:24][CH2:23]1>CN(C)C=O>[O:22]1[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][N:7]2[C:8]3[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=3[N:10]([CH3:13])[C:11](=[O:12])[C:5]3[C:4]([CH3:19])=[CH:3][C:2]([CH3:1])=[N:18][C:6]2=3)[CH2:24][CH2:23]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture consisting of 5.06 gm of 6,11-dihydro-2, 4,6-trimethyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, 1.1 gm of 50% sodium hydride in mineral oil and 60 ml of dimethyl formamide was stirred at 80° C. for 1 hour. Then, 4.5 gm of 2-morpholino-ethyl chloride were added, and the mixture was stirred at 120° C. for 3.5 hours more. The precipitate formed thereby was suction-filtered off, the solvent was removed from the filtrate in vacuo, and the oily residue was purified on a silica gel column. The product was recrystallized from petroleum ether (b.p. 100°-140° C.), yielding 64% of theory of the compound named in the heading, which had a melting point of 133°-135° C.

Workup

stirringthe mixture was stirred at 120° C. for 3.5 hours more
customThe precipitate formed
filtrationthereby was suction-filtered off
customthe solvent was removed from the filtrate in vacuo
customthe oily residue was purified on a silica gel column
customThe product was recrystallized from petroleum ether (b.p. 100°-140° C.)
customyielding 64% of theory of the compound

Sources & evidence

ORD record: ord-3dc766cdb09041f09d72be4764c046c3
Source dataset: uspto-grants-1979_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04167570

Reaction notes

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