Potassium Carbonate → HCID 70509492, compound

HRID 543711Notes

Reaction equation

HRID 543711 reaction equation
[CH:1]1[C:11]2[C:10](=[O:12])[NH:9][C:8]3[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.[CH3:18][N:19]1[CH2:27][CH2:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+].C(OC(C)C)(C)C.C(OCC)(=O)C>C1(C)C=CC=CC=1>[OH2:12].[CH3:18][N:19]1[CH2:27][CH2:26][C:22]([C:23]([N:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=3[C:10](=[O:12])[NH:9][C:8]3[CH:13]=[CH:14][CH:15]=[CH:16][C:7]2=3)=[O:24])=[CH:21][CH2:20]1.[CH3:18][N:19]1[CH2:27][CH2:26][C:22]([C:23]([N:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:11]=3[C:10](=[O:12])[NH:9][C:8]3[CH:13]=[CH:14][CH:15]=[CH:16][C:7]2=3)=[O:24])=[CH:21][CH2:20]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2013275,10-Dihydro-11H-dibenzo(b,e)(1,4)diazepin-11-oneHCID 13126595HCID 13126595, compoundHCID 22281796Diisopropylether ethyl acetate

Product 1

HCID 70509492HCID 70509492, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 10.65 g (0.051 mol) of 5,10-dihydro-11H-dibenzo[b,e][1,4]diazepin-11-one, 19.6 g (0.10 mol) of 1-methyl-1,2,5,6-tetrahydroisonicotinic acid chloride hydrochloride, 20.7 g (0.15 mol) of potassium carbonate and 200 ml of anhydrous toluene were refluxed for 24 hours, with thorough stirring. After cooling, the mixture was stirred into 500 ml of ice-cold water, the organic layer was separated off and the aqueous layer was exhaustively extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate then concentrated by evaporation in vacuo. The residue was purified by column chromatography, first on silica gel with a particle size of 0.1 to 0.4 mm, using 1,2-dichloroethane/methanol as eluant (ratio by volume 9:1), and secondly on silica gel with a particle size of from 0.05 to 0.2 mm, using 1,2-dichloroethane/methanol (volume ratio 95:5) as eluant. When the appropriate fractions were worked up in the usual way, colorless crystals were obtained, m.p. 233°-234° C. (diisopropylether/ethyl acetate). Yield: 2.4 g (14% of theory).

Workup

  1. temperaturewere refluxed for 24 hours, with thorough stirring
  2. temperatureAfter cooling
  3. customthe organic layer was separated off
  4. extractionthe aqueous layer was exhaustively extracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulphate
  6. concentrationthen concentrated by evaporation in vacuo
  7. customThe residue was purified by column chromatography, first on silica gel with a particle size of 0.1 to 0.4 mm
  8. customcolorless crystals were obtained

Sources & evidence

ORD record
ord-ea940a0ba2434bcc9215501848af489b
Source dataset
uspto-grants-1984_05
Patent number
US04447434

Reaction notes

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