Acetic Acid → HCID 178423777, compound

HRID 1497414Notes

Reaction equation

HRID 1497414 reaction equation
[Na].[CH3:2][C:3]1([CH3:11])[CH2:7][CH2:6][CH:5]([CH:8]=O)[C:4]1=O.[C:12]([CH2:14][C:15]([NH2:17])=[O:16])#[N:13].N1CCCCC1.C(O)(=O)C>O>[OH:16][C:15]1[N:17]=[C:4]2[C:3]([CH3:11])([CH3:2])[CH2:7][CH2:6][C:5]2=[CH:8][C:14]=1[C:12]#[N:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7898CyanoacetamideHCID 8082PiperidineHCID 89407569HCID 89407569, compound

Product 1

HCID 178423777HCID 178423777, compoundYield 13.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3,3-dimethyl-2-oxocyclopentanecarbaldehyde sodium salt (5 g, 30.9 mmol) in water (10 mL) was added cyanoacetamide (2.5 g, 30.9 mmol), piperidine (2.6 g, 30.9 mmol in 10 mL water) and acetic acid (1 mL) in that order. The reaction mixture was stirred at 100° C. for about 26 h and then cooled to a temperature of about 20-35° C. The reaction mass was adjusted to pH value of about 6 and was then filtered off to obtain a crude product. The crude product was purified by column chromatography (60-120 mesh silica gel) with 10% ethyl acetate in petroleum ether as the eluent to obtain the desired product as a brown liquid (0.8 g).

Workup

  1. temperaturecooled to a temperature of about 20-35° C
  2. filtrationwas then filtered off
  3. customto obtain a crude product
  4. customThe crude product was purified by column chromatography (60-120 mesh silica gel) with 10% ethyl acetate in petroleum ether as the eluent

Sources & evidence

ORD record
ord-7495c2d96162423f8d4b63b7d4bf06ce
Source dataset
uspto-grants-2015_12
Patent number
US09199967B2

Reaction notes

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