Cyclohexyl isocyanate → HCID 12148996, compound

HRID 1836404Notes

Reaction equation

HRID 1836404 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]1([N:23]=[C:24]=[O:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>C(Cl)Cl.C(O)(=O)C.CO>[CH:17]1([NH:23][C:24](=[O:25])[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])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 2

HCID 18502Cyclohexyl isocyanate2×HCID 101306514-[3-Aminobenzoyl]-1-methylpiperidine

Product 1

HCID 12148996HCID 12148996, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

4-[3-aminobenzoyl]-1-methylpiperidine (25 mg, 0.115 mmol) and cyclohexyl isocyanate (44 μL, 0.344 mmol) in methylene chloride (2 mL) were mixed for 72 h at ambient temperature. The 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 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 dissolved in tetrahydrofuran (2 mL). Cyclohexyl isocyanate (44 μL, 0.344 mmol) and poly(4-dimethyaminopyridine) (82 mg, 0.115 mmol) were added and the reaction mixture was mixed for 5 days. The reaction mixture was filtered and the filter cake was washed with methanol. The 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 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 to give 36.4 mg (93%) of the title compound.

Workup

  1. additionpoured over a Varian Mega Bond Elut™ strong cation exchange column
  2. washThe column was rinsed extensively with methanol
  3. customto remove impurities
  4. additiontreated with a 2M ammonia in methanol
  5. washto elute the product from the column
  6. customThe solvent was evaporated
  7. dissolutionthe residue was dissolved in tetrahydrofuran (2 mL)
  8. additionthe reaction mixture was mixed for 5 days
  9. filtrationThe reaction mixture was filtered
  10. washthe filter cake was washed with methanol
  11. additionThe solution was diluted with 10% acetic acid in methanol
  12. additionpoured over a Varian Mega Bond Elut™ strong cation exchange column
  13. washThe column was rinsed extensively with methanol
  14. customto remove impurities
  15. additiontreated with a 2M ammonia in methanol
  16. washto elute the product from the column
  17. customThe solvent was evaporated

Sources & evidence

ORD record
ord-5d33df7491d849c9a8769b1f59984937
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

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