1-[3-(4-Benzyloxy-phenoxy)-propyl]-piperidine → 4-(3-Piperidin-1-yl-propoxy)-phenol

HRID 33696Notes

Reaction equation

HRID 33696 reaction equation
C([O:8][C:9]1[CH:24]=[CH:23][C:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CO>[N:17]1([CH2:16][CH2:15][CH2:14][O:13][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:24][CH:23]=2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 2

HCID 25809111-[3-(4-Benzyloxy-phenoxy)-propyl]-piperidineHCID 2723923Ammonium formate

Product 1

HCID 179626194-(3-Piperidin-1-yl-propoxy)-phenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
68 °C

Procedure

A suspension of the product of Example 6 (2.5 g), ammonium formate (2.7 g), and 10% palladium on carbon (2.5 g) in methanol (100 mL) was heated in a 68° C. bath for 3 h, and allowed to cool to room temperature. The mixture was filtered through Celite, and the filtrate was evaporated in vacuo. Saturated aqueous sodium bicarbonate was added, and the mixture was extracted with dichloromethane (4×30 mL). The combined organic phases were dried (magnesium sulfate) and evaporated in vacuo, yielding the title compound as a pink microcrystalline solid (1.3 g) which was used without further purification. A small sample (100 mg) was recrystallized (ethanol) to obtain the title compound as beige prisms (68 mg).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe mixture was filtered through Celite
  3. customthe filtrate was evaporated in vacuo
  4. additionSaturated aqueous sodium bicarbonate was added
  5. extractionthe mixture was extracted with dichloromethane (4×30 mL)
  6. dry with materialThe combined organic phases were dried (magnesium sulfate)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-81ee811f926f41be8980b67c4fd6e802
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

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