Butyl Isothiocyanate → HCID 23518809, compound

HRID 1836409Notes

Reaction equation

HRID 1836409 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].[CH2:17]([N:21]=[C:22]=[S:23])[CH2:18][CH2:19][CH3:20].C=CC1C=CC=CC=1.C=CC1C=CC(C=C)=CC=1.C=CC1C=CC=C(C=C)C=1.C=CC1C(C=C)=CC=CC=1>O1CCCC1>[CH2:17]([NH:21][C:22](=[S:23])[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])[CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 11613Butyl Isothiocyanate2×HCID 101306514-[3-Aminobenzoyl]-1-methylpiperidineHCID 16211260HCID 16211260, compound

Product 1

HCID 23518809HCID 23518809, compound

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. Butyl isothiocyanate (41 μL, 0.344 mmol) was added and the reaction mixture was mixed for 96 h at ambient temperature. An addition amount of butyl isothiocyanate (100 μL, 0.829 mmol) was added to the reaction mixture and mixing was continued for another 6 days. Polystyrene methylisocyanate (230 mg, 0.230 mmol, 1% crosslinked poly(styrene-co-divinylbenzene) was added, and the reaction mixture was mixed 7 days 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 radial chromatography (silica gel, 1000 micron rotor, methylene chloride:2M ammonia in methanol, 100:2 then 100:4). The solvent was concentrated in vacuo to give 20.3 (53%) of the title compound.

Workup

  1. additionthe reaction mixture was mixed for 96 h at ambient temperature
  2. additionmixing
  3. waitwas continued for another 6 days
  4. additionwas added
  5. additionthe reaction mixture was mixed 7 days at ambient temperature
  6. filtrationThe reaction mixture was filtered
  7. washthe filter cake was rinsed with methanol
  8. additionGlacial acetic acid (0.5 mL) was added to the filtrate solution
  9. additionthe solution was mixed
  10. additionThis mixture was poured over a Varian Mega Bond Elut™ strong cation exchange column
  11. washThe column was rinsed extensively with methanol
  12. customto remove impurities
  13. additiontreated with a 2M ammonia in methanol
  14. washto elute the product from the column
  15. customThe solvent was evaporated
  16. customthe residue was purified by radial chromatography (silica gel, 1000 micron rotor, methylene chloride
  17. concentrationThe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-f73af28be760453b96b9d16a91ad0e13
Source dataset
uspto-grants-2004_08
Patent number
US06777428B1

Reaction notes

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