Triethylamine → HCID 86609416, compound

HRID 1171646Notes

Reaction equation

HRID 1171646 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3](/[CH:7]=[C:8]2\[CH2:9][N:10]([C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:11][CH2:12][CH:13]\2O)[CH:2]=1.CS(Cl)(=O)=O.C(N(CC)CC)C.[C:46]([O-:49])(=[S:48])[CH3:47].[K+]>ClCCl.C(OCC)(=O)C>[C:46]([S:48][CH:13]1[CH2:12][CH2:11][N:10]([C:15]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:9]/[C:8]/1=[CH:7]\[C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)(=[O:49])[CH3:47]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23139007HCID 23139007, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 86609416HCID 86609416, compoundYield 43.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (E)-3-[(pyridin-3-yl)methylidene]-1-(triphenylmethyl)piperidin-4-ol (5.40 g) in dichloromethane (85 ml) were added successively methanesulfonyl chloride (1.93 ml) and triethylamine (3.49 ml) under ice-cooling, and the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was evaporated in vacuo, and the residue was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated in vacuo. Subsequently, to a solution of the residue thus obtained in dimethyl sulfoxide (75 ml) was added potassium thioacetate (7.10 g) at room temperature, and the resulting mixture was stirred at 40° C. for 1 hour. The reaction mixture was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate. The solvent was removed, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (1:9) as the eluent to afford the title compound (2.68 g, yield: 42%) as a pale brown amorphous solid.

Workup

  1. temperaturecooling
  2. customThe reaction mixture was evaporated in vacuo
  3. additionthe residue was diluted with ethyl acetate
  4. washwashed with saturated aqueous sodium chloride solution
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customSubsequently, to a solution of the residue thus obtained in dimethyl sulfoxide (75 ml)
  8. stirringthe resulting mixture was stirred at 40° C. for 1 hour
  9. washwashed with saturated aqueous sodium chloride solution
  10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  11. customThe solvent was removed
  12. customthe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-4a6949148c714552a096187d283c4ab8
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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