4-Chlorophenyl Isocyanate → HCID 22676578, compound

HRID 1006382Notes

Reaction equation

HRID 1006382 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[O:10])=[CH:4][CH:3]=1.[CH2:11]([CH:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][CH2:26][NH:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[ClH:1].[CH2:11]([CH:18]1[CH2:19][CH2:20][N:21]([CH2:24][CH2:25][CH2:26][N:27]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)[C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:10])[CH2:22][CH2:23]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 76934-Chlorophenyl IsocyanateHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 22676614HCID 22676614, compound

Product 1

HCID 22676578HCID 22676578, compoundYield 114.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chlorophenyl isocyanate (297 mg) was added to a solution of N-[3-(4-benzyl-1-piperidinyl)propyl]-3-pyridineamine (400 mg) in tetrahydrofuran (5 ml) and the mixture was stirred for 15 hours. Ethyl acetate (15 ml) and saturated sodium bicarbonate (15 ml) were added to the reaction mixture. The organic phase was separated, washed with water (10 ml) and saturated brine (10 ml) and dried over sodium sulfate (anhydrous), and the solvent was removed. The residue was purified by silica gel column chromatography (20 g). The fraction eluted by ethyl acetate-methanol (10:1) was collected and concentrated under reduced pressure. A solution of 4N hydrogen chloride in ethyl acetate (1.0 ml) was added to the residue. The precipitate was filtered and collected, and dried under reduced pressure to give the title compound (555 mg, Yield 76.0%).

Workup

  1. customThe organic phase was separated
  2. washwashed with water (10 ml) and saturated brine (10 ml)
  3. dry with materialdried over sodium sulfate (anhydrous)
  4. customthe solvent was removed
  5. customThe residue was purified by silica gel column chromatography (20 g)
  6. washThe fraction eluted by ethyl acetate-methanol (10:1)
  7. customwas collected
  8. concentrationconcentrated under reduced pressure
  9. additionA solution of 4N hydrogen chloride in ethyl acetate (1.0 ml) was added to the residue
  10. filtrationThe precipitate was filtered
  11. customcollected
  12. customdried under reduced pressure

Sources & evidence

ORD record
ord-7af758bd23084449aefd79554a52656e
Source dataset
uspto-grants-2004_09
Patent number
US06787650B1

Reaction notes

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