Pyridine → HCID 19045359, compound

HRID 1591169Notes

Reaction equation

HRID 1591169 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:16][C:9]3([CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]3)[CH2:8][C:7](=[O:17])[C:6]=2[CH:18]=1.N1C=CC=CC=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>C(Cl)Cl>[CH3:25][S:26]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:16][C:9]3([CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]3)[CH2:8][C:7](=[O:17])[C:6]=2[CH:18]=1)(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 19045276HCID 19045276, compound

Product 1

HCID 19045359HCID 19045359, compoundYield 419%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,4-Dihydro-6-amino-1'-methyl-spiro[2H-1-benzopyran-2,4'-piperidin]-4-one (5.6 g, 0.0027 mol) was stirred in methylene chloride (50 ml) and pyridine (16 ml) at room temperature under a nitrogen atmosphere as methanesulfonyl chloride (2.7 ml, 0.035 mol) was added dropwise over several minutes. Some gum separated so additional pyridine (25 ml) was added. The mixture was stirred at ambient temperature for 16 hours. The methylene chloride and pyridine were removed in vacuo and the residue was taken up in saturated NaHCO3 (150 ml) and methylene chloride (150 ml). The methylene chloride layer was separated and the aqueous phase was again extracted with methylene chloride. The combined extracts were washed with sodium bicarbonate, dried filtered and concentrated in vacuo. The residual mixture was chromatographed on silica gel (500 g) using 15% methanol/chloroform to yield 3.67 g (50%) of product.

Workup

  1. customSome gum separated so additional pyridine (25 ml)
  2. additionwas added
  3. customThe methylene chloride and pyridine were removed in vacuo
  4. customThe methylene chloride layer was separated
  5. extractionthe aqueous phase was again extracted with methylene chloride
  6. washThe combined extracts were washed with sodium bicarbonate
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residual mixture was chromatographed on silica gel (500 g)

Sources & evidence

ORD record
ord-73088e84a49b41ac8624f269b413fafd
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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