Piperidine → HCID 69516430, compound

HRID 458407Notes

Reaction equation

HRID 458407 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=O)=[CH:6][CH:5]=1)([OH:3])=[O:2].[F:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][C:21](=[O:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:15][CH:14]=1.N1CCCCC1>C1C=CC=CC=1>[CH2:26]([O:25][C:23]([C:22]([C:21](=[O:28])[CH2:20][CH2:19][C:16]1[CH:15]=[CH:14][C:13]([F:12])=[CH:18][CH:17]=1)=[CH:8][C:7]1[CH:10]=[CH:11][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=1)=[O:24])[CH3:27]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 120884-Formylbenzoic acidHCID 11436342498532-06-2

Product 1

HCID 69516430HCID 69516430, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4-carboxybenzaldehyde (2.07 g, 13.81 mmol), ethyl 5-(4-fluorophenyl)-3-oxopentanoate (3.29 g, 13.81 mmol) and piperidine (0.25 mL, 2.53 mmol) in benzene (60 mL) was heated at reflux overnight under Dean-Stark conditions. The reaction mixture was concentrated and the crude material was dissolved in EtOAc. The EtOAc solution was washed with 0.1 M HCl and brine and then dried, filtered, and concentrated. Recrystallization of the resulting material from EtOAc/hexanes produced the title compound as a yellow solid (1.3 g, 3.51 mmol, 25%): 1H NMR (400 MHz, CDCl3) δ 8.09 (d, 2H, J=8), 7.98 (d, 2H, J=8), 7.70 (s, 1H), 7.60 (s, 1H), 7.49 (d, 2H, J=8), 7.32 (d, 2H, J=8), 7.16 (dd, 2H, J=8, 6), 7.07 (dd, 2H, J=8, 6), 6.97 (t, 2H, J˜9), 6.91 (t, 2H, J˜9), 4.29 (q, 2H, J=7), 4.27 (q, 2H, J=7), 3.03 (m, 2H), 2.99 (m, 2H), 2.90 (m, 2H), 2.84 (m, 2H), 1.29 (t, 3H, J=7), 1.23 (t, 3H, J=7) ppm (carboxyl proton not found).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight under Dean-Stark conditions
  3. concentrationThe reaction mixture was concentrated
  4. dissolutionthe crude material was dissolved in EtOAc
  5. washThe EtOAc solution was washed with 0.1 M HCl and brine
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customRecrystallization of the resulting material from EtOAc/hexanes

Sources & evidence

ORD record
ord-26efb4084bae4c9882fbd4bbcb96d45a
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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