Diethyl Ether → HCID 6918426, compound

HRID 1955218Notes

Reaction equation

HRID 1955218 reaction equation
[ClH:1].[OH:2][C:3]1([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(N1C[CH2:28][C:27](CC2C=CC(C)=CC=2)([OH:30])[CH2:26][CH2:25]1)C1C=CC=CC=1.[CH3:39][CH2:40][O:41][CH2:42][CH3:43]>C(O)C.[Pd]>[ClH:1].[OH:30][C:27]1[CH:26]=[CH:25][C:40]([O:41][CH2:42][CH2:43][N:6]2[CH2:7][CH2:8][C:3]([OH:2])([CH2:9][C:10]3[CH:11]=[CH:12][C:13]([CH3:16])=[CH:14][CH:15]=3)[CH2:4][CH2:5]2)=[CH:39][CH:28]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 105926411-Benzyl-4-(4-methylbenzyl)piperidin-4-olHCID 226283764-[(4-Methylphenyl)methyl]piperidin-4-ol hydrochloride

Product 1

HCID 6918426HCID 6918426, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-Hydroxy-4-(4-methylbenzyl)piperidine hydrochloride. A mixture of 1-benzyl-4-(4-methylbenzyl)-4-hydroxypiperidine (2.8 g, 9.5 mmol) and 700 mg of 10% Pd/C in 100 mL of 95% ethanol was hydrogenated at 50 psi for overnight. The catalyst was removed through a short column of celite (10 g) and washed with methanol (3×15 mL). To the filtrate was added 12 mL of 1M HCl in methanol. Evaporation of methanol gave a residue, to which was added 30 mL of ether. The mixture was stirred at rt for 2 days. A white solid was collected by filtration, giving 2.1 g (92%) of the title product. mp 183-185° C. 1H NMR (CDCl3) 1.680 (m, 2 H), 2.097 (m, 2 H), 2.338 (s, 3 H), 2.783 (s, 2 H), 3.241 (m, 5 H), 7.049 (d, J=7.5 Hz, 2 H), 7.142 (d, J=7.5 Hz, 2 H), 9.30 (brs, 1 H), 9.515 (brs, 1 H).

Workup

  1. customThe catalyst was removed through a short column of celite (10 g)
  2. washwashed with methanol (3×15 mL)
  3. additionTo the filtrate was added 12 mL of 1M HCl in methanol
  4. customEvaporation of methanol
  5. customgave a residue
  6. filtrationA white solid was collected by filtration

Sources & evidence

ORD record
ord-1999d381c970477ea6f7f857c4928f35
Source dataset
uspto-grants-2000_09
Patent number
US06124323

Reaction notes

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