Dimethylformamide → Hydrocarbostyril

HRID 1377731Notes

Reaction equation

HRID 1377731 reaction equation
Cl.N1CCC(OC2C=CC(C(N3CCC([N:21]4[C:30]5[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=5)[CH2:24][CH2:23][C:22]4=[O:31])CC3)=O)=C(OC)C=2)CC1.CN(C=O)C.ClCC#N>C(=O)([O-])[O-].[K+].[K+]>[NH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23][C:22]1=[O:31]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7856ChloroacetonitrileHCID 22914658HCID 22914658, compound

Product 1

HCID 64796Hydrocarbostyril

Reagents, catalysts & solvents 1

HCID 11430Potassium CarbonateSolvent

Conditions

Temperature
0 °C

Procedure

1-(1-(4-(4-Piperidinyloxy)-2-methoxybenzoyl)piperidin-4-yl)-3,4-dihydro-2(1H)-quinolinone hydrochloride from Example 190 (500 mg, 1.00 mmole) was dissolved in 7 ml of dry DMF containing 303 mg (2.19 mmole) of potassium carbonate. The suspension was cooled to 0° C. and 90 gL (1.42 mmole) of chloroacetonitrile was added neat with stirring. The cooling bath was removed after 10 minutes and the reaction was continued at room temperature for 4 hr. All volatiles were rotoevaporated and the residue was partitioned between ethyl acetate and brine. The combined organic extracts were dried and concentrated to yield 430 mg of 1-(1-(4-(N-cyanomethyl)piperidin-4-yloxy)-2-methoxybenzoyl) piperidin-4-yl)-3,4-dihydro-2(1H)-quinolinone as an oil.

Workup

  1. customThe cooling bath was removed after 10 minutes
  2. customthe residue was partitioned between ethyl acetate and brine
  3. customThe combined organic extracts were dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-8e674fb3beaf4de197082cf3476ee830
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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