HCID 19834275, compound → HCID 19834276, compound

HRID 1723354Notes

Reaction equation

HRID 1723354 reaction equation
[ClH:1].C([O:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[C:13]([O:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15]2)C1C=CC=CC=1>C(O)C.[Pd]>[ClH:1].[OH:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[C:13]([O:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[C:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15]2

Participants

4

Reactant 1

HCID 19834275HCID 19834275, compound

Product 1

HCID 19834276HCID 19834276, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 8.8 g (0.019 mole) of ethyl 5-benzyloxy-3-(2-piperidinoethoxy)-2-naphthoate hydrochloride in 240 cc ethanol was treated with 1.0 g of 10 percent palladium on carbon and hydrogenated at room temperature. The reaction mixture was filtered and the solvent removed in vacuo. The residue, weighing 7.5 g on recrystallization from acetonitrile furnished ethyl 5-hydroxy-3-(2-piperidinoethoxy)-2-naphthoatehydrochloride, m.p. 153° C.-6° C. in 61 percent yield (4.4 g).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent removed in vacuo
  3. customon recrystallization from acetonitrile

Sources & evidence

ORD record
ord-50e2c23dcde6441aa24baf9b1ad08225
Source dataset
uspto-grants-1989_08
Patent number
US04861795

Reaction notes

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