Water → 1-[4-(3-Mercaptopropylamino)phenyl]-2-dimethylamino-2-benzyl-propan-1-one

HRID 376964Notes

Reaction equation

HRID 376964 reaction equation
I[CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:25])[C:13]([N:22]([CH3:24])[CH3:23])([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:14])=[CH:8][CH:7]=1.C([O-])(=[S:28])C.[K+].O>CC(N(C)C)=O>[SH:28][CH2:2][CH2:3][CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:25])[C:13]([N:22]([CH3:24])[CH3:23])([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:14])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 193605911-[4-(3-Iodopropylamino)phenyl]-2-dimethylamino-2-benzyl-propan-1-oneHCID 23670855Potassium ethanethioate

Product 1

HCID 193606141-[4-(3-Mercaptopropylamino)phenyl]-2-dimethylamino-2-benzyl-propan-1-one

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

6.6 g (0.015 mol) of 1-[4-(3-Iodopropylamino)phenyl]-2-dimethylamino-2-benzyl-propan-1-one are dissolved in 50 ml of dimethylacetamide. To the solution are added 2.42 g of potassium thioacetate and heated up to 50° C. After the reaction mixture is stirred at 50° C. for 2 h, it is poured into 100 ml of water and extracted with ethyl acetate. The organic phase is washed with water and saturated sodium chloride solution, and dried over MgSO4. After distilling off the ethyl acetate, the residue is dissolved in 70 ml of ethanol and the solution is bubbled by nitrogen for 30 min. to remove oxygen. To the solution are added 7 ml of 2 N sodium hydroxide solution and stirred at 0° C. for 30 min. After the reaction mixture is neutralized by adding 2 N hydrochloric acid solution, the resulting solution is poured into 100 ml of water and extracted with ethyl acetate. The organic phase is washed with water and saturated sodium chloride 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 (1:2) as an eluent, and an oily product is obtained. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm]: 1.14 (s, 3H), 1.43 (t, 1H), 1.97 (m, 2H), 2.33 (s, 6H), 2.68 (q, 2H), 2.96 (d, 1H), 3.34-3.39 (m, 2H), 3.42 (d, 1H), 4.18 (br, 1H), 6.57 (d, 2H), 6.89-6.92 (m, 2H), 7.10-7.12 (m, 3H), 8.46 (d, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with water and saturated sodium chloride solution
  3. dry with materialdried over MgSO4
  4. distillationAfter distilling off the ethyl acetate
  5. dissolutionthe residue is dissolved in 70 ml of ethanol
  6. customthe solution is bubbled by nitrogen for 30 min.
  7. customto remove oxygen
  8. additionTo the solution are added 7 ml of 2 N sodium hydroxide solution
  9. stirringstirred at 0° C. for 30 min
  10. additionby adding 2 N hydrochloric acid solution
  11. additionthe resulting solution is poured into 100 ml of water
  12. extractionextracted with ethyl acetate
  13. washThe organic phase is washed with water and saturated sodium chloride solution
  14. dry with materialdried over MgSO4
  15. distillationAfter ethyl acetate is distilled off
  16. customthe residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:2) as an eluent
  17. customan oily product is obtained

Sources & evidence

ORD record
ord-730daac8153a40778431b66b3df9abe3
Source dataset
uspto-grants-2000_02
Patent number
US06022906

Reaction notes

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