Methyl 6-chloro-5-nitronicotinate → Methyl 6-(2-(methoxycarbonyl)piperidin-1-yl)-5-nitronicotinate

HRID 716244

Reaction equation

HRID 716244 reaction equation
Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[NH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]1[C:21]([O:23][CH3:24])=[O:22]>ClCCl>[CH3:24][O:23][C:21]([CH:16]1[CH2:17][CH2:18][CH2:19][CH2:20][N:15]1[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1)=[O:22]

Participants

4

Reactant 2

HCID 346961Methyl 6-chloro-5-nitronicotinateHCID 3463753Methyl pipecolinate

Product 1

HCID 58324403Methyl 6-(2-(methoxycarbonyl)piperidin-1-yl)-5-nitronicotinateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 6-chloro-5-nitronicotinate (2.0 g, 9.23 mmol) was added to methyl piperidine-2-carboxylate (5.2 g, 36.92 mmol) while stirring at room temperature. The viscous yellow reaction was heated to 90° C. for one h and then allowed to cool back to room temperature. The reaction was diluted with dichloromethane (20 mL) and purified via column chromatography (220 g SiO2, 20-30% gradient, ethyl acetate in hexanes) to yield the title compound (2.95 g, 99% yield) as a yellow oil. [M+H] calc'd for C14H17N3O6, 324. found, 324.

Workup

  1. customThe viscous yellow reaction
  2. temperaturewas heated to 90° C. for one h
  3. temperatureto cool back to room temperature
  4. custompurified via column chromatography (220 g SiO2, 20-30% gradient, ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-68cbb686c28540b9aac9f1ba27ee8fe5
Source dataset
uspto-grants-2015_11
Patent number
US09187497B2

Linked notes

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