Potassium Carbonate → Diisopropylether methanol

HRID 2295282Notes

Reaction equation

HRID 2295282 reaction equation
N1C2N[C:8]3[CH:16]=[CH:15]C=CC=3[C:10](=[O:12])NC=2C=CC=1.Cl.CN1C[CH2:26][C:22]([C:23](Cl)=O)=CC1.C(=O)([O-])[O-:29].[K+].[K+]>C1(C)C=CC=CC=1>[CH:22]([O:29][CH:16]([CH3:15])[CH3:8])([CH3:23])[CH3:26].[CH3:10][OH:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 701695,11-Dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-oneHCID 13126595HCID 13126595, compound

Product 1

HCID 21882575Diisopropylether methanol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 10.6 gm (0.05 mol) of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one, 10.8 gm (0.055 mol) of 1-methyl-1,2,5,6-tetrahydroisonicotinic acid chloride hydrochloride, 20.7 gm (0.15 mol) of potassium carbonate, and 200 ml of anhydrous toluene was refluxed for 48 hours under thorough stirring. After the mixture cooled, it was stirred into 500 ml of ice 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 and then concentrated by evaporation in vacuo. The residue was purified by column chromatography, first on silica gel with a particle size of from 0.1 to 0.4 mm, 1,2-dichloroethane/methanol (volume ratio of 9:1) being used as eluant, and secondly on silica gel with a particle size of from 0.032 to 0.063 mm, methylene chloride/methanol (volume ratio of 10:1) being used as eluant. The appropriate fractions were worked up in the usual way to produce colorless crystals, m.p.: 226°-227° C. (diisopropylether/methanol).

Workup

  1. temperaturewas refluxed for 48 hours under thorough stirring
  2. temperatureAfter the mixture cooled
  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. concentrationconcentrated by evaporation in vacuo
  7. customThe residue was purified by column chromatography, first on silica gel with a particle size of from 0.1 to 0.4 mm, 1,2-dichloroethane/methanol (volume ratio of 9:1)

Sources & evidence

ORD record
ord-9a6626c624c640dd8bba8bbcf3591e5e
Source dataset
uspto-grants-1984_01
Patent number
US04424226

Reaction notes

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