Methanol → HCID 12783758, compound

HRID 1979774Notes

Reaction equation

HRID 1979774 reaction equation
[Cl:1][C:2]1[C:3]([OH:14])=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[NH:8][C:7](=[O:13])[CH2:6][CH2:5]2.[OH-].[K+].CO.Cl[CH2:20][CH:21]([CH3:35])[CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:25][CH2:24]1>CN(C)C=O>[Cl:1][C:2]1[C:3]([O:14][CH2:20][CH:21]([CH3:35])[CH2:22][N:23]2[CH2:24][CH2:25][CH:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:27][CH2:28]2)=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[NH:8][C:7](=[O:13])[CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 887MethanolHCID 14797Potassium HydroxideHCID 12783756HCID 12783756, compoundHCID 12899417HCID 12899417, compound

Product 1

HCID 12783758HCID 12783758, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.4 Grams of 6,8-dichloro-5-hydroxy-3,4-dihydrocarbostyril and 0.8 g of granular potassium hydroxide were mixed with 60 ml of methanol and concentrated under a reduced pressure to dryness. To the residue thus obtained was added 60 ml of dimethylformamide and mixed well, then 5 g of 1-chloro-2-methyl-3-(4-phenylpiperidyl)propane and heated at 70°-80° C. for 8 hours under stirring condition. The reaction mixture was concentrated under a reduced pressure to dryness, then 60 ml of 5% sodium hydrogencarbonate aqueous solution was added thereto and extracted with chloroform. The chloroform layer was washed with water and dried, then the chloroform was removed by distillation and thus obtained residue was purified by silica-gel column chromatography and recrystallized from ligroin to obtain 1.6 g (yield: 35%) of 6,8-dichloro-5-[2-methyl-3-(4-phenyl-1-piperidyl)propoxy]-3,4-dihydrocarbostyril as in the form of colorless needle-like crystals. Melting point 125°-126° C.

Workup

  1. concentrationconcentrated under a reduced pressure to dryness
  2. customTo the residue thus obtained
  3. additionmixed well
  4. concentrationThe reaction mixture was concentrated under a reduced pressure to dryness
  5. addition60 ml of 5% sodium hydrogencarbonate aqueous solution was added
  6. extractionextracted with chloroform
  7. washThe chloroform layer was washed with water
  8. customdried
  9. customthe chloroform was removed by distillation and thus obtained residue
  10. customwas purified by silica-gel column chromatography
  11. customrecrystallized from ligroin

Sources & evidence

ORD record
ord-eefae3bc23ca410c95d5b97f4982e968
Source dataset
uspto-grants-1984_11
Patent number
US04482560

Reaction notes

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