Formaldehyde → HCID 22457754, compound

HRID 2184725Notes

Reaction equation

HRID 2184725 reaction equation
[O:1]=[C:2]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[CH2:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].C=O.N1CCCC[CH2:19]1>C(OCC)(=O)C>[N:12]1[CH:13]=[CH:14][CH:15]=[C:10]([C:2]([C:3](=[CH2:19])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:1])[CH:11]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 4248889Ethyl 4-oxo-4-(pyridin-3-yl)butanoate

Product 1

HCID 22457754HCID 22457754, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 4-oxo-4-(3-pyridyl)butanoate (4 g), 37% aqueous formaldehyde (2.46 g) and piperidine (2.46 g) was stirred at room temperature for 18 h. The reaction mixture was diluted with 200 mL of ethyl acetate and washed with water (2×100 mL). The reaction mixture was concentrated and dissolved in ethanol (10 mL) and treated with 4N HCl/dioxane (4 mL) at 80° C. for 12 h. The reaction mixture was diluted with ethyl acetate (200 mL), washed with water (2×100 mL), saturated sodium bicarbonate solution (2×100 mL), concentrated and purified on flash chromatography (20% Ethyl acetate to 80% ethyl acetate in hexane) to give 2.28 g of the title compound, ESMS (M+1)+220.

Workup

  1. washwashed with water (2×100 mL)
  2. concentrationThe reaction mixture was concentrated
  3. dissolutiondissolved in ethanol (10 mL)
  4. additiontreated with 4N HCl/dioxane (4 mL) at 80° C. for 12 h
  5. additionThe reaction mixture was diluted with ethyl acetate (200 mL)
  6. washwashed with water (2×100 mL), saturated sodium bicarbonate solution (2×100 mL)
  7. concentrationconcentrated
  8. custompurified on flash chromatography (20% Ethyl acetate to 80% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f2dc5fef7e564b51869e660838e2ebb0
Source dataset
uspto-grants-2002_06
Patent number
US06399606B1

Reaction notes

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