HCID 70047987, compound → HCID 70046612, compound

HRID 1419901Notes

Reaction equation

HRID 1419901 reaction equation
[CH2:1]([C:8]1([OH:34])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:33])[C:19]2[CH:24]=[CH:23][C:22]([O:25]CC3C=CC=CC=3)=[CH:21][CH:20]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(O)(=O)C>[CH2:1]([C:8]1([OH:34])[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:33])[C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 70047987HCID 70047987, compound

Product 1

HCID 70046612HCID 70046612, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Palladium on carbon (10%, 50 mg) was added to a solution of N-[3-(4-benzyl-4-hydroxy-piperidin-1-yl)-propyl]-4-benzyloxy-benzamide (185 mg, 0.40 mmol) in acetic acid (5 ml). The hydrogenation was complete after 4 h. The catalyst was removed by filtration through celite and the solvent was evaporated. Sodium bicarbonate (10% aq. solution, 2 ml) was added, and the aqeous layer extracted with dichloromethane. The organic layer was dried (Na2SO4), filtered and evaporated to give N-[3-(4-benzyl-4-hydroxy-piperidin-1-yl)-propyl]-4-hydroxy-benzamide (130 mg, 87%) as a white solid. MS: me/e=369 (M+H)+.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. customthe solvent was evaporated
  3. additionSodium bicarbonate (10% aq. solution, 2 ml) was added
  4. extractionthe aqeous layer extracted with dichloromethane
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-ce863281a0af41d68fa75422ead0485f
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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