Acetic Acid → HCID 86608808, compound

HRID 1987765Notes

Reaction equation

HRID 1987765 reaction equation
[NH2:1][C:2]1[CH:29]([CH3:30])[CH:6]2[CH2:7][C:8]([CH2:11][C:12]3[CH2:13][CH2:14][N:15]([C:18]4[CH:23]=[CH:22][C:21]([N:24]5[CH:28]=[CH:27][N:26]=[CH:25]5)=[CH:20][CH:19]=4)[CH2:16][CH:17]=3)([CH3:10])[O:9][C:5]2=[C:4]([CH3:31])[C:3]=1[CH3:32].C(O)C.C(O)(=O)C.[OH-].[Na+]>[C].[Pd].O>[NH2:1][C:2]1[CH:29]([CH3:30])[CH:6]2[CH2:7][C:8]([CH2:11][CH:12]3[CH2:17][CH2:16][N:15]([C:18]4[CH:19]=[CH:20][C:21]([N:24]5[CH:28]=[CH:27][N:26]=[CH:25]5)=[CH:22][CH:23]=4)[CH2:14][CH2:13]3)([CH3:10])[O:9][C:5]2=[C:4]([CH3:31])[C:3]=1[CH3:32]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 86608806HCID 86608806, compound

Product 1

HCID 86608808HCID 86608808, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

In an autoclave, to 0.45 g of 4-(±)-(5-amino-2,4,6,7-tetramethyldihydrobenzofuran-2-ylmethyl)-1-(4-imidazol-1-ylphenyl)-1,2,3,6-tetrahydropyridine and 0.1 g of 10% palladium carbon, 5 ml of ethanol and 5 ml of acetic acid were added, followed by stirring at 50° C. under a hydrogen pressure of 10 kg/cm2 for 7 hours. The reaction solution was poured into water, neutralized with 1N sodium hydroxide solution and then extracted with chloroform. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration and concentrating under reduced pressure, the resulting crystal was washed with hexane and then dried to obtain 0.39 g of the objective product (mp: 170-172° C.).

Workup

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing magnesium sulfate
  5. filtrationby filtration
  6. concentrationconcentrating under reduced pressure
  7. washthe resulting crystal was washed with hexane
  8. customdried

Sources & evidence

ORD record
ord-e9f8fd9181534e4f9ca2131f002f4637
Source dataset
uspto-grants-2009_06
Patent number
US07553837B2

Reaction notes

Loading…