Diethyl Ether → HCID 6918426, compound

HRID 1594630Notes

Reaction equation

HRID 1594630 reaction equation
[ClH:1].C([O:9][C:10]1[CH:33]=[CH:32][C:13]([O:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][C:20]([OH:31])([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)=[CH:12][CH:11]=1)C1C=CC=CC=1.[H][H].CCOCC>CO.[OH-].[OH-].[Pd+2]>[ClH:1].[OH:9][C:10]1[CH:11]=[CH:12][C:13]([O:14][CH2:15][CH2:16][N:17]2[CH2:18][CH2:19][C:20]([OH:31])([CH2:23][C:24]3[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=3)[CH2:21][CH2:22]2)=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 69704311193357-90-3HCID 178418361HCID 178418361, compound

Product 1

HCID 6918426HCID 6918426, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

1-[2-(4-Hydroxyphenoxy)ethyl]-1-hydroxy-4-(4-methylbenzyl)piperidine hydrochloride. To a solution of 1-[2-(4-benzyloxyphenoxy)ethyl]-4-hydroxy-4-(4-methylbenzyl)piperidine hydrochloride (0.25 g, 0.53 mmol) in 30 mL of methanol was added 62.5 mg of 20% Pd(OH)2. The resulting mixture was hydrogenated at 20 psi of hydrogen for 3 h. The catalyst was removed through a short column of celite (5 g) and washed with methanol (3×15 mL). Methanol was evaporated in vacuo to give a residue, to which 50 mL of ether was added. The resulting mixture was stirred overnight. A white solid was collected by filtration and dried in vacuo, giving 200 mg (100%) of the title product: mp 133-135° C.

Workup

  1. customThe catalyst was removed through a short column of celite (5 g)
  2. washwashed with methanol (3×15 mL)
  3. customMethanol was evaporated in vacuo
  4. customto give a residue
  5. filtrationA white solid was collected by filtration
  6. customdried in vacuo

Sources & evidence

ORD record
ord-3e2219c55b03447e9696e49ae9e1576d
Source dataset
uspto-grants-2001_09
Patent number
US06284776B1

Reaction notes

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