Pyridinium, 4-methyl-1-(phenylmethyl)-, chloride (1:1) → 1-Benzyl-4-methyl-1,2,3,6-tetrahydropyridine

HRID 734773Notes

Reaction equation

HRID 734773 reaction equation
[Cl-].[CH2:2]([N+:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCOC(C)=O.CO.N>>[CH2:2]([N:9]1[CH2:10][CH:11]=[C:12]([CH3:15])[CH2:13][CH2:14]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 10856996Pyridinium, 4-methyl-1-(phenylmethyl)-, chloride (1:1)HCID 21873639Ethyl acetate methanol ammonia

Product 1

HCID 64215721-Benzyl-4-methyl-1,2,3,6-tetrahydropyridine

Procedure

The product was obtained analogously to IP 5b starting from 10.0 g (45.5 mmol) of 1-benzyl-4-methylpyridinium chloride. Yield: 7.15 g (84% of theoretical); C13H17N (M=187.281); calc.: molpeak (M+H)+: 188; found: molpeak (M+H)+: 188; Rf value: 0.95 (silica gel, EtOAc/MeOH/NH3 9:1:0.1).

Sources & evidence

ORD record
ord-e3ad53ba131b46f0af5d55816a809fb8
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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