Piperidine → HCID 69590310, compound

HRID 890163Notes

Reaction equation

HRID 890163 reaction equation
[C:1]([O:7][CH2:8][CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:6])[CH2:2][C:3]([CH3:5])=O.[Cl:17][C:18]1[CH:19]=[C:20]([CH:23]=C[CH:25]=1)C=O.[NH:26]1CCC[CH2:28][CH2:27]1.[C:32]([O:36][CH2:37][CH2:38][C:39]#[N:40])(=[O:35])[C:33]#[CH:34].C([O-])(=O)C.[NH4+]>C1C=CC=CC=1.C(O)(=O)C.O>[Cl:17][C:18]1[CH:25]=[C:5]([CH:3]2[C:33]([C:32]([O:36][CH2:37][CH2:38][C:39]#[N:40])=[O:35])=[CH:34][NH:26][C:27]([CH3:28])=[C:2]2[C:1]([O:7][CH2:8][CH:9]=[CH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:6])[CH:23]=[CH:20][CH:19]=1

Participants

9

Reactant 5

HCID 8082PiperidineHCID 114773-ChlorobenzaldehydeHCID 937263-Phenyl-2-propen-1-yl 3-oxobutanoateHCID 517165Ammonium AcetateHCID 204932242-Cyanoethyl prop-2-ynoate

Product 1

HCID 69590310HCID 69590310, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

655 mg (3.0 mmol) of cinnamyl acetoacetate, 0.34 ml (3.0 mmol) of 3-chlorobenzaldehyde and 0.0297 ml of piperidine were heated under reflux in 3.0 ml of benzene overnight while water was removed. The reaction liquid was washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was heated to 70° C. together with 370 mg (3.0 mmol) of (2-cyanoethyl) propiolate and 232 mg (3.0 mmol) of ammonium acetate under stirring in 3 ml of acetic acid for two nights. Acetic acid was evaporated under reduced pressure, and the residue was purified by the silica gel chromatography (hexane/ethyl acetate=3/2) to obtain the title compound.

Workup

  1. customwas removed
  2. customThe reaction liquid
  3. washwas washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customAcetic acid was evaporated under reduced pressure
  7. customthe residue was purified by the silica gel chromatography (hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-0e300d8d7d0b4acfb11904bdc3326333
Source dataset
uspto-grants-2006_02
Patent number
US06995179B2

Reaction notes

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