Isopropyl isocyanate → HCID 23499364, compound

HRID 1836407Notes

Reaction equation

HRID 1836407 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].[CH:17]([N:20]=[C:21]=[O:22])([CH3:19])[CH3:18]>O1CCCC1>[CH:17]([NH:20][C:21](=[O:22])[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])([CH3:19])[CH3:18]

Participants

4

Reactant 2

HCID 61277Isopropyl isocyanateHCID 101306514-[3-Aminobenzoyl]-1-methylpiperidine

Product 1

HCID 23499364HCID 23499364, compoundYield 63%

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. Isopropyl isocyanate (34 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 (1-3% gradient, 2M ammonia in methanol:methylene chloride). The solvent was evaporated to give 21.8 mg (63%) 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 (1-3% gradient, 2M ammonia in methanol:methylene chloride)
  13. customThe solvent was evaporated

Sources & evidence

ORD record
ord-07f0e0e5db19447886b1e29504845110
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

Loading…