Diethyl Ether → 1-benzyl-4-[N-(4-n-butoxyphenyl)-N-methylaminomethyl]piperidin-4-ol

HRID 49962Notes

Reaction equation

HRID 49962 reaction equation
[O-2].[Al+3].[O-2].[O-2].[Al+3].C(OCC)C.[CH2:11]([N:18]1[CH2:25][CH2:24][C:21]2([CH2:23][O:22]2)[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH2:26]([O:30][C:31]1[CH:38]=[CH:37][C:34]([NH:35][CH3:36])=[CH:33][CH:32]=1)[CH2:27][CH2:28][CH3:29]>CO>[CH2:11]([N:18]1[CH2:25][CH2:24][C:21]([CH2:23][N:35]([C:34]2[CH:37]=[CH:38][C:31]([O:30][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:32][CH:33]=2)[CH3:36])([OH:22])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 31989Aniline, p-butoxy-N-methyl-HCID 892386-Benzyl-1-oxa-6-azaspiro(2,5)octaneHCID 9989226Alumina

Product 1

HCID 178237981-benzyl-4-[N-(4-n-butoxyphenyl)-N-methylaminomethyl]piperidin-4-olYield 75.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Activated neutral aluminum oxide 90 (activity I, made by Merck Co.) (5 g) was added to a diethyl ether solution (10 mL) of 1-benzylpiperidin-4-spiro-2′-oxirane (0.50 g) and 4-butoxy-N-methylaniline (0.53 g) and stirred at room temperature overnight. Methanol (20 mL) was added to the reaction solution and stirred at room temperature for 2 hours. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. The residue obtained was purified by silica gel column chromatography (elution solvent; ethyl acetate) to obtain the titled compound (0.71 g).

Workup

  1. stirringstirred at room temperature for 2 hours
  2. filtrationThe reaction solution was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue obtained
  5. customwas purified by silica gel column chromatography (elution solvent; ethyl acetate)

Sources & evidence

ORD record
ord-3ded8f04c190456d870ee3eaca6c19b5
Source dataset
uspto-grants-2004_03
Patent number
US06710060B2

Reaction notes

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