Diethyl Ether → 11-(2'-dimethylamino-ethyl)-6,11-dihydro-6-methyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one
Reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[NH:6][C:5]2[N:13]=[CH:14][CH:15]=[CH:16][C:4]=2[C:3]1=[O:17].[H-].[Na+].[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23]Cl.CCOCC>C1(C)C(C)=CC=CC=1.O>[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][N:6]1[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[N:2]([CH3:1])[C:3](=[O:17])[C:4]2[CH:16]=[CH:15][CH:14]=[N:13][C:5]1=2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
9.0 gm of 6,11-dihydro-6-methyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one were dissolved in 200 ml of hot absolute xylene, 2.1 gm of 50% sodium hydride in mineral oil were added to the solution, and the mixture was refluxed for 2 hours. Then, 5.3 gm of 2-dimethylamino-ethyl chloride were added dropwise, and the mixture was refluxed for 16 hours more. The cooled reaction mixture was shaken with a mixture of ether and water, and the organic phase was separated and extracted with dilute acetic acid. Then the acidic aqueous layer was made alkaline with concentrated ammonia, and the precipitated oil was extracted with ether. After evaporation of the ether extract, the residue was distilled, yielding 7.0 gm (59% of theory) of 11-(2'-dimethylamino-ethyl)-6,11-dihydro-6-methyl-5H-pyrido[2,3-b][1,5]benzodiazepin-5-one, b.p. 163°-164° C. at 0.01 mm Hg.
Workup
- temperaturethe mixture was refluxed for 2 hours
- temperaturethe mixture was refluxed for 16 hours more
- customThe cooled reaction mixture
- customthe organic phase was separated
- extractionextracted with dilute acetic acid
- extractionthe precipitated oil was extracted with ether
- customAfter evaporation of the ether
- extractionextract
- distillationthe residue was distilled
Sources & evidence
- ORD record
- ord-6eca6ee8c19e40d08f75de47021d5d63
- Source dataset
- uspto-grants-1977_05
- Patent number
- US04021557
Reaction notes
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