Piperidine → HCID 12148994, compound

HRID 1836380Notes

Reaction equation

HRID 1836380 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.[N+:23]([C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][CH:27]=1)([O-:25])=[O:24]>O1CCCC1>[N+:23]([C:26]1[CH:27]=[CH:28][C:29]([C:30]([NH:1][C:2]2[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=2)[C:5]([CH:7]2[CH2:8][CH2:9][N:10]([CH3:13])[CH2:11][CH2:12]2)=[O:6])=[O:31])=[CH:33][CH:34]=1)([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 85024-Nitrobenzoyl chlorideHCID 101306514-[3-Aminobenzoyl]-1-methylpiperidine

Product 1

HCID 12148994HCID 12148994, compoundYield 110.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 4-[3-aminobenzoyl]-1-methylpiperidine (50 mg, 0.229 mmol) and (piperidinomethyl)-polystyrene (176 mg, 0.458 mmol) in tetrahydrofuran (1 mL) was added 4-nitrobenzoyl chloride (85 mg, 0.458 mmol) in tetrahydrofuran (1 mL). The reaction mixture was mixed for 18 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. 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 93 mg (>100%) of the title compound.

Workup

  1. additionThe reaction mixture was mixed for 18 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
  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-e6b4a06f2da549a2bef8ec972a121e54
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

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