Lithium Hydroxide → HCID 58002414, compound

HRID 1642803Notes

Reaction equation

HRID 1642803 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][NH:14][CH2:13][CH:12]([C:16]([O:18]CC)=[O:17])[CH2:11]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH:28]1([C:33](Cl)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1.[OH-].[Li+]>ClCCl.O.O1CCOCC1>[CH:28]1([C:33]([N:14]2[CH2:15][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][CH3:2])=[CH:9][CH:8]=3)[CH2:11][CH:12]([C:16]([OH:18])=[O:17])[CH2:13]2)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

8

Reactant 4

HCID 3939Lithium HydroxideHCID 8471TriethylamineHCID 78284Cyclopentanecarbonyl chlorideHCID 66755335HCID 66755335, compound

Product 1

HCID 58002414HCID 58002414, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

0.83 g (3.05 mmol) of ethyl 5-(4-methoxyphenyl)piperidine-3-carboxylate hydrochloride was dissolved in 10 ml of dichloromethane, and 0.77 g (7.62 mmol) of triethylamine was added at 0° C. 0.83 g (6.09 mmol) of cyclopentanecarbonyl chloride was then added dropwise. The reaction mixture was stirred at RT for 2 h. For work-up, the mixture was twice washed with water. The organic phase was dried over sodium sulphate and concentrated under reduced pressure. 35 ml of dioxane, 17.5 ml of water and 0.29 mg (12.2 mmol) of lithium hydroxide were added to the crude product. The mixture was stirred at RT for 1 h. For work-up, the dioxane was removed under reduced pressure, water was added and the reaction mixture was acidified using aqueous 1 N hydrochloric acid solution. The precipitated solid was filtered off and dried under reduced pressure. Yield: 0.84 g (75% of theory)

Workup

  1. washFor work-up, the mixture was twice washed with water
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. stirringThe mixture was stirred at RT for 1 h
  5. customFor work-up, the dioxane was removed under reduced pressure, water
  6. additionwas added
  7. filtrationThe precipitated solid was filtered off
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-0e676b31204047858e5a45632125f6e0
Source dataset
uspto-grants-2012_02
Patent number
US08119663B2

Reaction notes

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