Piperidine → HCID 66892646, compound

HRID 1028242Notes

Reaction equation

HRID 1028242 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([CH2:13][C:14]#[N:15])[C:3]=1[C:16]#[N:17].[CH3:18][O:19][C:20]1[CH:27]=[CH:26][CH:25]=[C:24]([O:28][CH3:29])[C:21]=1[CH:22]=O.N1CCCCC1>C1(C)C=CC=CC=1>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([C:13]([C:14]#[N:15])=[CH:22][C:21]2[C:24]([O:28][CH3:29])=[CH:25][CH:26]=[CH:27][C:20]=2[O:19][CH3:18])[C:3]=1[C:16]#[N:17]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 81585NSC22494HCID 964042,6-Dimethoxybenzaldehyde

Product 1

HCID 66892646HCID 66892646, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1 g (4.48 mmol) of 5-amino-4-cyano-1-phenyl-3-pyrazoleacetonitrile is suspended in 15 mL of toluene, in a round-bottomed flask, under an argon atmosphere, surmonted by a Dean and Stark apparatus. 0.744 g (1 eq.) of 2,6-dimethoxybenzaldehyde and 0.030 mL of piperidine are added to the mixture. The reaction medium is refluxed overnight, and is then allowed to return to ambient temperature. A whitish precipitate forms and is filtered off and washed with toluene. The filtrate is concentrated to dryness and the residue is taken up in ethanol with agitation for 15 minutes. The suspension is filtered and the filtrate is concentrated to dryness. The residue is combined with the precipitate previously obtained, and purified on silica gel (eluent: 98/2 dichloromethane/methanol). 619 mg of product are thus obtained with a yield of 37%.

Workup

  1. temperatureThe reaction medium is refluxed overnight
  2. customto return to ambient temperature
  3. filtrationA whitish precipitate forms and is filtered off
  4. washwashed with toluene
  5. concentrationThe filtrate is concentrated to dryness
  6. filtrationThe suspension is filtered
  7. concentrationthe filtrate is concentrated to dryness
  8. custompreviously obtained
  9. custompurified on silica gel (eluent: 98/2 dichloromethane/methanol)

Sources & evidence

ORD record
ord-dd9a567cb7214b66a88df72963445129
Source dataset
uspto-grants-2014_05
Patent number
US08735445B2

Reaction notes

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