Water → HCID 12813961, compound

HRID 1576244Notes

Reaction equation

[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[N:12]([CH3:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]([C:17]([O:19][CH3:20])=[O:18])[C:4]=2[CH:3]=1.[CH3:21][N:22]([CH3:26])[CH2:23][CH2:24]Cl.O>O1CCCC1>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[N:12]([CH3:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([C:17]([O:19][CH3:20])=[O:18])([CH2:24][CH2:23][N:22]([CH3:26])[CH3:21])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 45 °C

Procedure

3.9 gm of 2-chloro-9-methoxycarbonyl-10-methyl-acridane were dissolved in 10 cc of tetrahydrofuran and 5 cc of hexamethyl phosphortriamide and the solution was heated to 45°C and 3.4 gm of potassium tert.-butylate were added thereto. After stirring the mixture for 1 hour at 45°-47°C, 4.5 gm of β-dimethylaminoethyl chloride were added thereto and the mixture was stirred for 16 hours at 46°-48°C. After cooling the mixture, 150 cc of water were added and the mixture was extracted with ether. The organic phases were washed with an aqueous solution of sodium chloride, dried over magnesium sulfate, treated with charcoal, filtered and evaporated to dryness to obtain 4.2 gm of raw 2-chloro-9-methoxycarbonyl-9-(β-dimethylaminoethyl)-10-methyl-acridane.

Workup

stirringthe mixture was stirred for 16 hours at 46°-48°C
additionwere added
extractionthe mixture was extracted with ether
washThe organic phases were washed with an aqueous solution of sodium chloride
dry with materialdried over magnesium sulfate
additiontreated with charcoal
filtrationfiltered
customevaporated to dryness

Sources & evidence

ORD record: ord-d0200d31ab0c4bd1b0441fbc7d4ade0e
Source dataset: uspto-grants-1976_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03979515

Reaction notes

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