Dimethyl Sulfate → 2-(3-Hydroxy-1,2,3,4-tetrahydronaphthalenyl)-1-methylpiperidine

HRID 46504Notes

Reaction equation

HRID 46504 reaction equation
[OH:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH2:3]1.S(OC)(O[CH3:22])(=O)=O>CC(O)=O.O=[Pt]=O.[Pd]>[OH:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([CH:12]2[CH2:17][CH2:16][CH2:15][CH2:14][N:13]2[CH3:22])[CH2:3]1

Participants

6

Reactant 2

HCID 6497Dimethyl SulfateHCID 203873802-(3-Hydroxy-1,2,3,4-tetrahydronaphthalenyl)-pyridine

Product 1

HCID 203873702-(3-Hydroxy-1,2,3,4-tetrahydronaphthalenyl)-1-methylpiperidine

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolvent

Procedure

The 2-(3-hydroxy-1,2,3,4-tetrahydronaphthalenyl)-pyridine thus obtained is quaternized with dimethyl sulfate on the steam bath neat. After several hours, the salt is dissolved in HOAc and reduced over a mixture of PtO2 and Pd/C to yield 2-(3-hydroxy-1,2,3,4-tetrahydronaphthalenyl)-1-methyl piperidine.

Workup

  1. waitAfter several hours

Sources & evidence

ORD record
ord-2c2e83e84a6049d492ca1f0b4ece8da6
Source dataset
uspto-grants-1979_11
Patent number
US04173640

Reaction notes

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