Piperidine → HCID 12148993, compound

HRID 1836362Notes

Reaction equation

HRID 1836362 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([CH:7]1[CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]1)=[O:6].C1CCNCC1.[Br:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26](Cl)=[O:27]>C(Cl)Cl>[Br:23][C:24]1[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=1[C:26]([NH:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[C:5]([CH:7]1[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12]1)=[O:6])=[O:27]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 235422-Bromobenzoyl chlorideHCID 101306514-[3-Aminobenzoyl]-1-methylpiperidine

Product 1

HCID 12148993HCID 12148993, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-[3-aminobenzoyl]-1-methylpiperidine (50 mg, 0.229 mmol) and (piperidinomethyl)-polystyrene (100 mg, 0.260 mmol) in methylene chloride (1 mL) was allowed to stand for 5 min. To this mixture was added 2-bromobenzoyl chloride (151 mg, 0.687 mmol). The reaction mixture was mixed for 2 h at ambient temperature. The reaction mixture was filtered and the filter cake was rinsed with methanol. The filtrate solution was diluted with 10% acetic acid in methanol and poured over a Varian Mega Bond Elut™ strong cation exchange column (Siegel, M. G.; Hahn, P. J.; Dressman, B. A.; Fritz, J. E.; Grunwell, J. R.; Kaldor, S. W. Tetrahedron Lett. 1997, 38, 3357-3360). The column was rinsed with methanol to remove impurities, then treated with a 7M ammonia in methanol to elute the product from the column. The solvent was evaporated to give 45.6 mg (50%) of the title compound.

Workup

  1. additionThe reaction mixture was mixed for 2 h at ambient temperature
  2. filtrationThe reaction mixture was filtered
  3. washthe filter cake was rinsed with methanol
  4. additionThe filtrate solution was diluted with 10% acetic acid in methanol
  5. additionpoured over a Varian Mega Bond Elut™ strong cation exchange column (Siegel, M. G.; Hahn, P. J.; Dressman, B. A.; Fritz, J. E.; Grunwell, J. R.; Kaldor, S. W. Tetrahedron Lett. 1997, 38, 3357-3360)
  6. washThe column was rinsed with methanol
  7. customto remove impurities
  8. additiontreated with a 7M ammonia in methanol
  9. washto elute the product from the column
  10. customThe solvent was evaporated

Sources & evidence

ORD record
ord-015eb0c607be42719d548e3582c2467d
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

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