Thioanisole → HCID 18538495, compound

HRID 1394338Notes

Reaction equation

HRID 1394338 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](Cl)=[O:15])[CH2:10][CH2:9]1)(=[O:7])[CH3:6].[C:17]1([S:23][CH3:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>ClCCl>[C:5]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:15])[C:20]2[CH:21]=[CH:22][C:17]([S:23][CH3:24])=[CH:18][CH:19]=2)[CH2:10][CH2:9]1)(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 7520ThioanisoleHCID 1009501-Acetylpiperidine-4-carbonyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18538495HCID 18538495, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of aluminum chloride (16.66 g, 125 mmol) in dichloromethane (100 mL) was added 1-acetyl-4-piperidinecarbonyl chloride (12.33 g, 65.0 mmol) at −10° C. Thioanisole (6.21 g, 50.0 mmol) was added dropwise at −10° C., the reaction mixture was stirred at room temperature for 1.5 hours. The reaction mixture was poured into ice water (80 g), the organic layer was separated and the aqueous layer was extracted with dichloromethane (40 mL) The combined organic layers were washed with 1N aqueous sodium hydroxide (2×40 mL), brine (40 mL), dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure. Ethyl acetate and diethyl ether was added to the residue, the resulting precipitate was collected by filtration, washed with diethyl ether, and dried under reduced pressure to afford the title compound (11.43 g, 41.2 mmol, 82%) as a white solid.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer was extracted with dichloromethane (40 mL) The combined organic layers
  3. washwere washed with 1N aqueous sodium hydroxide (2×40 mL), brine (40 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. additionEthyl acetate and diethyl ether was added to the residue
  8. filtrationthe resulting precipitate was collected by filtration
  9. washwashed with diethyl ether
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-2cef58f7a40b40fdb9732e67786a1206
Source dataset
uspto-grants-2008_03
Patent number
US07348324B2

Reaction notes

Loading…