Piperidine → HCID 9845939, compound

HRID 1779955Notes

Reaction equation

HRID 1779955 reaction equation
[C:1]([O:7][CH:8]([CH3:10])[CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=O.N1CCCCC1.[CH2:17]([C:24]1[CH:25]=[N:26][C:27]2[CH:28]=[CH:29][CH:30]=[C:31]([CH:34]=O)[C:32]=2[CH:33]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[NH2:36]/[C:37](/[CH3:41])=[CH:38]\[C:39]#[N:40]>C(Cl)Cl.C(O)(=O)C>[C:39]([C:38]1[CH:34]([C:31]2[CH:30]=[CH:29][CH:28]=[C:27]3[C:32]=2[CH:33]=[C:24]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:25]=[N:26]3)[C:2]([C:1]([O:7][CH:8]([CH3:10])[CH3:9])=[O:6])=[C:3]([CH3:5])[NH:36][C:37]=1[CH3:41])#[N:40]

Participants

7

Reactant 4

HCID 8082PiperidineHCID 68329Isopropyl acetoacetateHCID 5325263(2Z)-3-Amino-2-butenenitrileHCID 15225072HCID 15225072, compound

Product 1

HCID 9845939HCID 9845939, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

0.72 g of isopropyl acetoacetate, 0.025 ml of acetic acid and 0.05 ml of piperidine are added to 1.24 g (5 mmol) of 3-benzylquinoline-5-aldehyde in 20 ml of methylene chloride and the mixture is heated at the boiling point overnight. It is cooled, diluted with methylene chloride, extracted twice by shaking with water, dried and concentrated. The resulting intermediate product is suspended in 15 ml of isopropanol, 0.41 g (5 mmol) of 3-aminocrotononitrile are added and the mixture is stirred at 80° C. for 20 hours. It is concentrated and the residue is purified by flash chromatography with toluene/ethyl acetate mixtures. After crystallization from ethanol/ether 1:1, 1.0 g of colourless crystals of melting point 188°-190° C. is obtained.

Workup

  1. temperaturethe mixture is heated at the boiling point overnight
  2. temperatureIt is cooled
  3. extractionextracted twice
  4. customdried
  5. concentrationconcentrated
  6. stirringthe mixture is stirred at 80° C. for 20 hours
  7. concentrationIt is concentrated
  8. customthe residue is purified by flash chromatography with toluene/ethyl acetate mixtures
  9. customAfter crystallization from ethanol/ether 1:1, 1.0 g of colourless crystals of melting point 188°-190° C.
  10. customis obtained

Sources & evidence

ORD record
ord-85aee255edd74e28a7b7a4fe236394ed
Source dataset
uspto-grants-1997_05
Patent number
US05629320

Reaction notes

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