Trifluoroacetic acid → 4-[(3,4-Dichlorophenyl)carbonyl]piperidine

HRID 369926Notes

Reaction equation

HRID 369926 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:22][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[Cl:21])[C:14]([CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)=[O:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 53945757Tert-butyl 4-(3,4-dichlorobenzoyl)piperidine-1-carboxylate

Product 1

HCID 124044204-[(3,4-Dichlorophenyl)carbonyl]piperidineYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a room temperature solution of 4-(3,4-dichlorobenzoyl)piperidine-1-carboxylic acid tert-butyl ester (3.8 g, 10.6 mmol) in methylene chloride (100 mL) was added trifluoroacetic acid (25 mL) and the solution was stirred for 1 h. After removing the organics, ethyl acetate (200 mL) was added and the resulting solution was basified with 1N aqueous sodium hydroxide solution. The ethyl acetate layer was separated, dried with magnesium sulfate and concentrated to give 4-(3,4-dichlorobenzoyl)piperidine (2.73 g) as a white solid.

Workup

  1. customAfter removing the organics, ethyl acetate (200 mL)
  2. additionwas added
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2b92475429204c4cb48cf7e4bd5d6dee
Source dataset
uspto-grants-2000_10
Patent number
US06140344

Reaction notes

Loading…