Methylamine → HCID 86673553, compound

HRID 1190821Notes

Reaction equation

HRID 1190821 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]2[C:19]([N+:20]([O-:22])=[O:21])=[C:18](Cl)[N:17]=[C:16]([O:24][CH:25]=[O:26])[CH:15]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:28][NH2:29]>C(O)C>[C:1]([O:5][C:6](=[O:27])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]2[C:19]([N+:20]([O-:22])=[O:21])=[C:18]([NH:29][CH3:28])[N:17]=[C:16]([O:24][CH:25]=[O:26])[CH:15]=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 86673554HCID 86673554, compound

Product 1

HCID 86673553HCID 86673553, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a dry reaction bottle, 16 g (R)-1-[2-formyloxy-5-nitro-6-chloropyridin-4-yl]piperidine-3-carbamic acid tert-butyl ester (40 mmol) was added and dissolved in 50 mL ethanol. 31 g 40% methylamine aqueous solution (400 mmol) was added. The stirring was continued for 2 days at 60° C. The reaction solution was extracted with dichloromethane, dried, and evaporated to dryness to afford a crude product as yellow solid, which was purified through a column chromatography (ethyl acetate:petroleum ether=1:1) to afford 12 g titled product with a yield of 75.9%.

Workup

  1. additionwas added
  2. extractionThe reaction solution was extracted with dichloromethane
  3. customdried
  4. customevaporated to dryness
  5. customto afford a crude product as yellow solid, which
  6. customwas purified through a column chromatography (ethyl acetate:petroleum ether=1:1)

Sources & evidence

ORD record
ord-7327c7e771ff4f31985e13b196adc988
Source dataset
uspto-grants-2014_03
Patent number
US08680089B2

Reaction notes

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