Potassium Carbonate → HCID 19360620, compound

HRID 376982Notes

Reaction equation

HRID 376982 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[C:9]([N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([CH2:18][OH:19])[CH2:13]2)([CH3:11])[CH3:10])=[CH:4][CH:3]=1.[SH:21][CH2:22][CH2:23][CH2:24][OH:25].C(=O)([O-])[O-].[K+].[K+]>CC(N(C)C)=O>[OH:25][CH2:24][CH2:23][CH2:22][S:21][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:20])[C:9]([N:12]2[CH2:17][CH2:16][CH2:15][CH:14]([CH2:18][OH:19])[CH2:13]2)([CH3:11])[CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 882113-MercaptopropanolHCID 19360593HCID 19360593, compound

Product 1

HCID 19360620HCID 19360620, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

22.4 g of 1-(4-chloro-phenyl)-2-(3-hydroxymethyl-piperidin-1-yl)-2-methyl-propan-1-one, 8.39 g of 3-mercaptopropanol and 21.0 g of potassium carbonate are mixed in 75 ml of dried dimethylacetamide. After stirring for 18 h at 80° C., the mixture is filtered to remove solids and poured into ice-water. The crude product is extracted with ethyl acetate, washed with saturated NaCl solution and dried over MgSO4. After ethyl acetate is distilled off, the residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (40:60) as an eluent, and an oily product is obtained. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 1.02 (m, 1H), 1.29 (s, 3H), 1.30 (s, 3H), 1.52-1.77 (m, 6H), 1.95 (m, 2H), 2.05 (t, 1H), 2.27 (t, 1H), 2.67 (d, 1H), 2.86 (d, 1H), 3.12 (t, 2H), 3.44 (m, 2H), 3.78 (m, 2H), 7.28 (d, 2H), 8.48 (d, 2H).

Workup

  1. filtrationthe mixture is filtered
  2. customto remove solids
  3. additionpoured into ice-water
  4. extractionThe crude product is extracted with ethyl acetate
  5. washwashed with saturated NaCl solution
  6. dry with materialdried over MgSO4
  7. distillationAfter ethyl acetate is distilled off
  8. customthe residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (40:60) as an eluent
  9. customan oily product is obtained

Sources & evidence

ORD record
ord-e577b32303ed4268b08c91335674aa3f
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Reaction notes

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