tert-Butyl 4-formylpiperidine-1-carboxylate → HCID 178456946, compound

HRID 1620498Notes

Reaction equation

HRID 1620498 reaction equation
[CH:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)=O.[CH2:16]([NH:19][C:20]1[CH2:24][S:23][C:22](=[O:25])[N:21]=1)[C:17]#[CH:18].C([O-])(=O)C.[NH2+]1CCCCC1>CC(O)C>[O:25]=[C:22]1[N:21]=[C:20]([NH:19][CH2:16][C:17]#[CH:18])/[C:24](=[CH:1]/[CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]2)/[S:23]1

Participants

5

Reactant 3

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 3014295Piperidinium acetateHCID 178456890HCID 178456890, compound

Product 1

HCID 178456946HCID 178456946, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 4-formylpiperidine-1-carboxylate (11.2 g) in 2-propanol (230 mL) were added 4-(prop-2-yn-1-ylamino)-1,3-thiazol-2(5H)-one (16.3 g) and piperidinium acetate (3.90 g). The reaction mixture was stirred at 60° C. overnight, and the solvent was evaporated under reduced pressure. Ethyl acetate was added to the residue, the precipitate was removed, and the filtrate was concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (14.0 g).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. customthe precipitate was removed
  4. concentrationthe filtrate was concentrated
  5. additionWater was added to the residue
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed with water and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2d1f4c70c0e44e019a253e196f4f8a92
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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