2-Chloro-5-nitrobenzoic acid → 2-(4-methylpiperidin-1-yl)-5-nitrobenzoic acid

HRID 1846100Notes

Reaction equation

HRID 1846100 reaction equation
Cl[C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>Cl>[CH3:14][CH:15]1[CH2:20][CH2:19][N:18]([C:2]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 172872-Chloro-5-nitrobenzoic acidHCID 693814-Methylpiperidine

Product 1

HCID 29434062-(4-methylpiperidin-1-yl)-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 10.0 g 2-chloro-5-nitro benzoic acid (50 mmol) and 13 mL 4-methyl-piperidine was refluxed for 2 h, 100 mL 1 N aq. HCl solution was added and it was extracted with 100 mL DCM. The organic phase was dried with Na2SO4, concentrated and purified via chromatography (silica gel, eluent: DCM:MeOH 100:1) to furnish the subtitle compound. MS [m+H]+=265.

Workup

  1. temperaturewas refluxed for 2 h
  2. extractionit was extracted with 100 mL DCM
  3. dry with materialThe organic phase was dried with Na2SO4
  4. concentrationconcentrated
  5. custompurified via chromatography (silica gel, eluent: DCM:MeOH 100:1)

Sources & evidence

ORD record
ord-a8bbd79263d64240b39da397353899f0
Source dataset
uspto-grants-2015_02
Patent number
US08951999B2

Reaction notes

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