Methanol → HCID 14576907, compound

HRID 1904626Notes

Reaction equation

HRID 1904626 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]([C:14]3[CH:19]=[CH:18][C:17]([S:20](C)(=O)=O)=[CH:16][CH:15]=3)[CH2:12][CH2:11][CH2:10][C:9]2=[O:24])=[CH:4][CH:3]=1.CO.C(N(CC)CC)C.[Cl-].[NH4+]>C(Cl)Cl.FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:13]([C:14]3[CH:15]=[CH:16][C:17]([SH:20])=[CH:18][CH:19]=3)[CH2:12][CH2:11][CH2:10][C:9]2=[O:24])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 14576906HCID 14576906, compound

Product 1

HCID 14576907HCID 14576907, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of 2.5 g of 1-(4-chlorophenyl)-6-(4-methylsulfonylphenyl)-2-piperidone in 10 ml of methylene chloride, 15 ml of anhydrous trifluoroacetic acid was added, and the mixture was refluxed at 45° C. for 3 hours. After cooling, 100 ml of a mixture of methanol and triethylamine (1:1) was added, and the mixture was stirred at room temperature for 1 hour and then treated with a saturated aqueous ammonium chloride solution. The methylene chloride layer was washed with water, dried, and evaporated to give 2.2 g of 1-(4-chlorophenyl)-6-(4-mercaptophenyl)-2-piperidone as pale yellow oily product.

Workup

  1. temperatureAfter cooling
  2. washThe methylene chloride layer was washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-8f1f7df4782349be935c78650d69b306
Source dataset
uspto-grants-1989_06
Patent number
US04839360

Reaction notes

Loading…