HCID 131715934, compound → HCID 21241513, compound

HRID 1761451Notes

Reaction equation

HRID 1761451 reaction equation
Cl.Cl.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:27]2([OH:33])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:12][CH2:13][N:14]2[CH2:19][CH2:18][N:17](CC3C=CC=CC=3)[CH2:16][CH2:15]2)=[CH:7][CH:6]=1>C(O)C.[Pd]>[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:27]2([OH:33])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]2)[CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 131715934HCID 131715934, compound

Product 1

HCID 21241513HCID 21241513, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-[1-(4-methoxyphenyl)-3-[4-(phenylmethyl)-1-piperazinyl]-1-propenyl]cyclohexanol, dihydrochloride (14.6 g, 29.6 mmole) in ethanol (250 mL) was hydrogenated in a Parr apparatus over 10% Pd/C for 65 hours. The catalyst was filtered and the filtrate evaporated. The residue was partitioned between ethyl acetate (120 mL) and N sodium hydroxide (65 mL). The layers were separated. The aqueous phase was extracted with ethyl acetate. The combined organic solution was washed with brine, dried over magnesium sulfate and evaporated to obtain the title compound as an oil. Wt. 7.8 g. Mass spectral analysis: Molecular weight by C.I.M.S.: M+1 334.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe filtrate evaporated
  3. customThe residue was partitioned between ethyl acetate (120 mL) and N sodium hydroxide (65 mL)
  4. customThe layers were separated
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washThe combined organic solution was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-2790ad0c4be84b11ae9eab226f137c55
Source dataset
uspto-grants-1989_05
Patent number
US04826844

Reaction notes

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