5-Bromo-2-fluorotoluene → Methyl N-(4-fluoro-3-methylphenyl)piperidine-4-carboxylate

HRID 1878506Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]1.Br[C:12]1[CH:13]=[CH:14][C:15]([F:19])=[C:16]([CH3:18])[CH:17]=1>>[F:19][C:15]1[CH:14]=[CH:13][C:12]([N:1]2[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH3:10])=[O:8])[CH2:3][CH2:2]2)=[CH:17][C:16]=1[CH3:18]

Participants

Reactant 2

HCID 1235275-Bromo-2-fluorotoluene

HCID 424914Methyl isonipecotate

Product 1

HCID 59023366Methyl N-(4-fluoro-3-methylphenyl)piperidine-4-carboxylate

Procedure

starting with 10.6 g (74.0 mmol) of methyl piperidine-4-carboxylate and 4.67 g (24.7 mmol) of 5-bromo-2-fluorotoluene, the general procedure [E] gives 2.74 g (40% of theory) of product.

Workup

customthe general procedure [E] gives 2.74 g (40% of theory) of product

Sources & evidence

ORD record: ord-6fea9c9e023a4d10aa16dcd7af1664c6
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08314113B2

Reaction notes

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