Chloroform → (6-Bromopyridin-3-yl)[4-(p-tolyloxy)piperidin-1-yl]methanone

HRID 1803965

Reaction equation

HRID 1803965 reaction equation
[C:1]1([CH3:14])[CH:6]=[CH:5][C:4]([O:7][CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:3][CH:2]=1.[Br:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][N:17]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.C(Cl)(Cl)Cl>CO>[Br:15][C:16]1[N:17]=[CH:18][C:19]([C:20]([N:11]2[CH2:12][CH2:13][CH:8]([O:7][C:4]3[CH:3]=[CH:2][C:1]([CH3:14])=[CH:6][CH:5]=3)[CH2:9][CH2:10]2)=[O:21])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 2389326-Bromonicotinic acidHCID 38374974-(4-Methylphenoxy)piperidineHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate

Product 1

HCID 58484591(6-Bromopyridin-3-yl)[4-(p-tolyloxy)piperidin-1-yl]methanoneYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 4-(p-tolyloxy)piperidine (765 mg), 6-bromonicotinic acid (808 mg) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (1.7 g) were added chloroform (5 mL) and methanol (5 mL), and the mixture was stirred at room temperature overnight. After evaporation of the solvent, the residue was purified by column chromatography (chloroform:methanol) to give the title compound (1.5 g).

Workup

  1. customAfter evaporation of the solvent
  2. customthe residue was purified by column chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-31d277f31d42413fbaa18166042e1a7d
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Linked notes

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