HCID 14456880, compound → HCID 53647417, compound

HRID 622632Notes

Reaction equation

HRID 622632 reaction equation
C1(C)C=CC(S([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][N:13]([CH:17]=[O:18])[CH2:12]2)(=O)=O)=CC=1.[C:20]([O-])(=[S:22])[CH3:21].[K+]>CN(C)C=O>[C:20]([O:10][CH:11]1[CH2:16][CH2:15][CH2:14][N:13]([CH:17]=[O:18])[CH2:12]1)(=[S:22])[CH3:21]

Participants

4

Reactant 2

HCID 14456880HCID 14456880, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 53647417HCID 53647417, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-formyl-3-piperidinyl p-toluenesulfonate (1.12 g., 0.007 mole) and potassium thioacetate (0.91 g., 0.008 mole) in 10 ml. dimethylformamide was heated at 70° C. under nitrogen for 20 hours. The reaction mixture was diluted with 150 ml. ethyl acetate and the resulting solution was washed with four 50 ml. portions of water and 50 ml. brine, dried over anhydrous sodium acetate and concentrated in vacuo. The residue was chromatographed on silica gel (125 g.) eluting with 4:1 ethyl acetate-hexane to yield 0.16 g. (21% yield) of the title compound. NMR (CDCl3): 1.13-2.3 (c) and 2.32 (s) (total 7H); 2.84-4.0 (c, 5H); and 7.9 (d, 1H)ppm.

Workup

  1. additionThe reaction mixture was diluted with 150 ml
  2. washethyl acetate and the resulting solution was washed with four 50 ml
  3. dry with materialbrine, dried over anhydrous sodium acetate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (125 g.)
  6. washeluting with 4:1 ethyl acetate-hexane
  7. customto yield 0.16 g

Sources & evidence

ORD record
ord-5fa8eb8e77514202ba2f3ca187f08960
Source dataset
uspto-grants-1988_09
Patent number
US04772597

Reaction notes

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