Methyl Isocyanate → HCID 12148997, compound

HRID 1836408Notes

Reaction equation

HRID 1836408 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].[CH3:17][N:18]=[C:19]=[O:20]>O1CCCC1>[CH3:17][NH:18][C:19](=[O:20])[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]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 101306514-[3-Aminobenzoyl]-1-methylpiperidine

Product 1

HCID 12148997HCID 12148997, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[3-aminobenzoyl]-1-methylpiperidine (25 mg, 0.115 mmol) and poly(4-vinyl pyridine) (50 mg, 0.400 mmol, 2% cross-linked) in tetrahydrofuran (2 mL) were allowed to stand 10 min. Methyl isocyanate (20 μL, 0.344 mmol) was added and the reaction mixture was mixed for 96 h at ambient temperature. The reaction mixture was filtered and the filter cake was rinsed with methanol. Glacial acetic acid (0.5 mL) was added to the filtrate solution and the solution was mixed. This mixture was poured over a Varian Mega Bond Elut™ strong cation exchange column. The column was rinsed extensively with methanol to remove impurities, then treated with a 2M ammonia in methanol to elute the product from the column. The solvent was evaporated and the residue was purified by silica gel chromatography (5% 2M ammonia in methanol:methylene chloride). The solvent was evaporated to give 28.1 mg (89%) of the title compound.

Workup

  1. additionthe reaction mixture was mixed for 96 h at ambient temperature
  2. filtrationThe reaction mixture was filtered
  3. washthe filter cake was rinsed with methanol
  4. additionGlacial acetic acid (0.5 mL) was added to the filtrate solution
  5. additionthe solution was mixed
  6. additionThis mixture was poured over a Varian Mega Bond Elut™ strong cation exchange column
  7. washThe column was rinsed extensively with methanol
  8. customto remove impurities
  9. additiontreated with a 2M ammonia in methanol
  10. washto elute the product from the column
  11. customThe solvent was evaporated
  12. customthe residue was purified by silica gel chromatography (5% 2M ammonia in methanol:methylene chloride)
  13. customThe solvent was evaporated

Sources & evidence

ORD record
ord-b130b125e40247158a82b3f80b9b2a3e
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

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