HCID 70045694, compound → HCID 70047761, compound

HRID 1419902Notes

Reaction equation

HRID 1419902 reaction equation
C([O:8][C:9]1[CH:35]=[CH:34][C:12]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][C:22]([OH:33])([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)[CH2:21][CH2:20]2)=[O:14])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(O)(=O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([NH:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][C:22]([OH:33])([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([CH3:32])=[CH:30][CH:31]=3)[CH2:21][CH2:20]2)=[O:14])=[CH:34][CH:35]=1

Participants

4

Reactant 1

HCID 70045694HCID 70045694, compound

Product 1

HCID 70047761HCID 70047761, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Palladium on carbon (10%, 50 mg) was added to a solution of 4-benzyloxy-N-[3-[4-hydroxy-4-(4-methyl-benzyl)-piperidin-1-yl]-propyl]-benzamide (220 mg, 0.46 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 4-hydroxy-N-[3-[4-hydroxy-4-(4-methyl-benzyl)-piperidin-1-yl]-propyl]-benzamide (178 mg,73%) as a white solid. MS: me/e=383 (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-7bf22fffe78b416bbe2ceb04ed7bcbd0
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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