HCID 18670458, compound → HCID 18670584, compound

HRID 1059365Notes

Reaction equation

HRID 1059365 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>C(O)C.[C].[Pd]>[NH:11]1[CH2:16][CH2:15][CH:14]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 1

HCID 18670458HCID 18670458, compound

Product 1

HCID 18670584HCID 18670584, compoundYield 78.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of 1.0 g of methyl 4-[1-(benzyloxy-carbonyl)piperidin-4-yl]phenylacetate in ethanol (100 ml) was added 1.0 g of 10% palladium-carbon (moisture content: 50%) and a hydrogenation reaction was effected under atmospheric pressure for 12 hours. Then the palladium-carbon was filtered off and the solvent was concentrated under reduced pressure to thereby give 0.5 g of crude methyl 4-(piperidin-4-yl)phenylacetate. To a solution of 0.5 g of this crude product and 0.5 g of 8-(chloroethyl)-10H-pyrazino[2,3-b][1,4]benzothiazine in N,N-dimethylformamide (30 ml) was added 0.87 g of anhydrous potassium carbonate and the resulting mixture was stirred under heating to 60° C. for 40 minutes. After adding water, the reaction mixture was extracted with ethyl acetate, washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel column chromatography (eluted with n-hexane/ethyl acetate) to thereby give 0.6 g of the title compound as a yellow oily substance.

Workup

  1. customa hydrogenation reaction
  2. filtrationThen the palladium-carbon was filtered off
  3. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5bc846acf6f24678afb71c3b5fc4becd
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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