rel-(2R,6S)-2,6-Dimethylpiperidine → 1-(2-(2,6-Dimethylpiperidyl)ethoxy)-4-((4-chloronaphthyloxy)methyl)benzene

HRID 353599Notes

Reaction equation

HRID 353599 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([Cl:23])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.[CH3:24][C@H:25]1[CH2:30][CH2:29][CH2:28][C@@H:27]([CH3:31])[NH:26]1>>[CH3:24][CH:25]1[CH2:30][CH2:29][CH2:28][CH:27]([CH3:31])[N:26]1[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][O:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16]([Cl:23])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 641768rel-(2R,6S)-2,6-DimethylpiperidineHCID 235143952-Chloro-1-(4-((4-chloronaphthyloxy)methyl)phenoxy)ethane

Product 1

HCID 235144091-(2-(2,6-Dimethylpiperidyl)ethoxy)-4-((4-chloronaphthyloxy)methyl)benzeneYield 47.2%

Procedure

A stirred mixture of 0.4 grams (0.001 mole) of 2-chloro-1-(4-((4-chloronaphthyloxy)methyl)phenoxy)ethane and 5 mL (0.037 mole) of cis-2,6-dimethylpiperidine was heated to just below reflux for about 72 hours. After this time, the reaction mixture was analyzed by thin layer chromatography (TLC), which indicated the reaction was incomplete. The reaction mixture was concentrated under reduced pressure and subject to column chromatography on silica gel, yielding 0.2 gram of compound 106. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturewas heated to just
  2. temperaturebelow reflux for about 72 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-dfc3d11ac59b486e8334a987f1fad1de
Source dataset
uspto-grants-2004_06
Patent number
US06753429B2

Reaction notes

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