Methanol → HCID 13363014, compound

HRID 1979778Notes

Reaction equation

HRID 1979778 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]2.[OH-].[K+].CO.Cl[CH2:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][C:24]([C:33](=[O:35])[CH3:34])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:23][CH2:22]1>CN(C)C=O>[C:33]([C:24]1([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:23][CH2:22][N:21]([CH2:20][CH2:19][CH2:18][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH:6]=[CH:5]3)[CH2:26][CH2:25]1)(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 1770652,6-DihydroxyquinolineHCID 20438562HCID 20438562, compound

Product 1

HCID 13363014HCID 13363014, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1.65 Grams of 6-hydroxycarbostyril and 0.75 g of granular potassium hydroxide were mixed with 50 ml of methanol and concentrated under a reduced pressure to dryness. To the residue obtained was added 50 ml of dimethylformamide and mixed well, then 2.6 g of 1-(3-chloropropyl)-4-acetyl-4-phenylpiperidine was added and heated at 50° C. for 6 hours under stirring condition. The reaction mixture was concentrated under a reduced pressure to dryness and 20 ml of 5%-sodium hydrogencarbonate aqueous solution was added thereto and stirred. The insoluble matters were collected by filtration and washed with water. After dried the insoluble matters were recrystallized from ethanol to obtain 1.1 g of 6-[3-(4-acetyl-4-phenyl-1-piperidyl)propoxy]carbostyril as in the form of colorless prism-like crystals. Melting point: 192.5°-194° C.

Workup

  1. concentrationconcentrated under a reduced pressure to dryness
  2. customTo the residue obtained
  3. additionmixed well
  4. concentrationThe reaction mixture was concentrated under a reduced pressure to dryness and 20 ml of 5%-sodium hydrogencarbonate aqueous solution
  5. additionwas added
  6. stirringstirred
  7. filtrationThe insoluble matters were collected by filtration
  8. washwashed with water
  9. customAfter dried the insoluble matters
  10. customwere recrystallized from ethanol

Sources & evidence

ORD record
ord-eda21df27e5d4f0eab459e0eb55d5a1d
Source dataset
uspto-grants-1984_11
Patent number
US04482560

Reaction notes

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