Formaldehyde → HCID 54234832, compound

HRID 1789927Notes

Reaction equation

HRID 1789927 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH:5]([CH:9]([C:13]1[CH:14]=[N:15][C:16]([NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:18]=1)[CH2:10][CH2:11][CH3:12])[C:6](O)=O)[CH3:2].C=O.N1CCCCC1>C1COCC1>[CH2:1]([O:3][C:4](=[O:26])[C:5]([CH:9]([C:13]1[CH:14]=[N:15][C:16]([NH:19][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:18]=1)[CH2:10][CH2:11][CH3:12])=[CH2:6])[CH3:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 69650218HCID 69650218, compound

Product 1

HCID 54234832HCID 54234832, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-{1-[6-(2,2-dimethyl-propionylamino)-pyridin-3-yl]-butyl}-malonic acid monoethyl ester (712 mg, 1.95 mmol) in THF (6.5 mL) at 0° C. formaldehyde (37% in water, 0.3 mL) was added within 5 min. Stirring was continued for 10 min, then piperidine (0.26 mL, 2.63 mmol) was added dropwise within 10 min. The mixture was allowed to warm up overnight to room temperature. After 14 h the mixture was concentrated under reduced pressure to one third of its volume, then ether and water were added (15 mL each). After 2 min vigorous stirring the layers were separated, the aqueous was extracted with ether and the combined organic layers were washed with water, 4% citric acid, water and brine. Drying and concentration under reduced pressure gave 2-{1-[6-(2,2-dimethyl-propionylamino)-pyridin-3-yl]-butyl}-acrylic acid ethyl ester (550 mg, 85%) as a colourless solid.

Workup

  1. temperatureto warm up overnight to room temperature
  2. concentrationAfter 14 h the mixture was concentrated under reduced pressure to one third of its volume
  3. additionether and water were added (15 mL each)
  4. stirringAfter 2 min vigorous stirring the layers
  5. customwere separated
  6. extractionthe aqueous was extracted with ether
  7. washthe combined organic layers were washed with water, 4% citric acid, water and brine
  8. customDrying
  9. concentrationconcentration under reduced pressure

Sources & evidence

ORD record
ord-7e95140ca4c5406b80a15afc1355eca2
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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