HCID 12751742, compound → 8-Phenylmethoxy-3,4-dihydro-5-[2-hydroxy-3-(4-(isobutoxycarbonylamino)-1-piperidyl)propoxy]carbostyril

HRID 1090706Notes

Reaction equation

HRID 1090706 reaction equation
[O:1]1[CH2:24][CH:2]1[CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:23])[NH:10]2.[NH:25]1[CH2:30][CH2:29][CH:28]([NH:31][C:32](=[O:38])[O:33][CH2:34][CH:35]([CH3:37])[CH3:36])[CH2:27][CH2:26]1>C(O)(C)C>[C:17]1([CH2:16][O:15][C:12]2[CH:13]=[CH:14][C:5]([O:4][CH2:3][CH:2]([OH:1])[CH2:24][N:25]3[CH2:26][CH2:27][CH:28]([NH:31][C:32]([O:33][CH2:34][CH:35]([CH3:37])[CH3:36])=[O:38])[CH2:29][CH2:30]3)=[C:6]3[C:11]=2[NH:10][C:9](=[O:23])[CH2:8][CH2:7]3)[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 12751742HCID 12751742, compoundHCID 15676964Isobutyl piperidin-4-ylcarbamate

Product 1

HCID 199137998-Phenylmethoxy-3,4-dihydro-5-[2-hydroxy-3-(4-(isobutoxycarbonylamino)-1-piperidyl)propoxy]carbostyrilYield 76.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5-(2,3-epoxypropoxy)-8-phenylmethoxy-3,4-dihydrocarbostyril (130 mg) was dissolved in isopropanol (10 mL) and isobutyl 4-piperidylcarbamate (80 mg) was added. The mixture was then heated under reflux for 20 hours with stirring. After completion of the reaction, the isopropanol was evaporated under reduced pressure. The residue was then purified by flash chromatography (AcOEt/MeOH-99:1) to yield 160 mg of the title compound, 8-phenylmethoxy-3,4-dihydro-5-[2-hydroxy-3-(4-(isobutoxycarbonylamino)-1-piperidyl)propoxy]carbostyril.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 20 hours
  3. customAfter completion of the reaction
  4. customthe isopropanol was evaporated under reduced pressure
  5. customThe residue was then purified by flash chromatography (AcOEt/MeOH-99:1)

Sources & evidence

ORD record
ord-b660a86f84c04dc596f3e522b8b77ded
Source dataset
uspto-grants-1992_01
Patent number
US05082847

Reaction notes

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