Formic Acid → HCID 21241518, compound

HRID 1761450Notes

Reaction equation

HRID 1761450 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]([C:25]2([OH:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[CH:10][CH2:11][N:12]2[CH2:17][CH2:16][N:15](CC3C=CC=CC=3)[CH2:14][CH2:13]2)[CH:6]=[CH:7][CH:8]=1.C([O-])=O.[Na+].C(O)=O>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]([C:25]2([OH:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]2)[CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][NH:15][CH2:16][CH2:17]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 2723810Sodium FormateHCID 54329946HCID 54329946, compound

Product 1

HCID 21241518HCID 21241518, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

A solution of 1-[1-(3-methoxyphenyl)-3-[4-(phenylmethyl)-1-piperazinyl]-1-propenyl]cyclohexanol (3.09 g, 7.1 mmole) in ethanol (50 mL) containing sodium formate (0.5 g, 7.1 mmole) and formic acid (1.5 g, 30 mmole) was added to a suspension of 10% Pd/C (3.0 g) in ethanol (50 mL) and the mixturre refluxed for 2 hours under nitrogen. The catalyst was filtered and the filtrate evaporated. The residue was partitioned between 4N sodium hydroxide (200 mL) and ethyl acetate (200 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.

Workup

  1. temperaturethe mixturre refluxed for 2 hours under nitrogen
  2. filtrationThe catalyst was filtered
  3. customthe filtrate evaporated
  4. customThe residue was partitioned between 4N sodium hydroxide (200 mL) and ethyl acetate (200 mL)
  5. customThe layers were separated
  6. extractionThe aqueous phase was extracted with ethyl acetate
  7. washThe combined organic solution was washed with brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-49f15bda23c84834ab7cc207e4bb15b4
Source dataset
uspto-grants-1989_05
Patent number
US04826844

Reaction notes

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