Trifluoroacetic acid → 1-(4-Cyclohexylpiperidin-4-yl)butan-1-one

HRID 333448Notes

Reaction equation

HRID 333448 reaction equation
[C:1]([C:6]1([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1)(=[O:5])[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O.[OH-].[Na+]>ClCCl>[CH:19]1([C:6]2([C:1](=[O:5])[CH2:2][CH2:3][CH3:4])[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 66987675Tert-butyl 4-butyryl-4-cyclohexylpiperidine-1-carboxylate

Product 1

HCID 669878491-(4-Cyclohexylpiperidin-4-yl)butan-1-oneYield 119.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.5 g (7.4 mmol) of tert-butyl 4-butyryl-4-cyclohexylpiperidine-1-carboxylate (cf. preparation 17-1-4) are diluted in a mixture comprising 40 mL of dichloromethane and 8 mL of trifluoroacetic acid. The mixture is stirred at room temperature for 2 hours and the reaction is then stopped by adding aqueous 1N NaOH solution and the organic compounds are extracted with dichloromethane. The organic phase is dried and then concentrated. 2.1 g of 1-(4-cyclohexylpiperidin-4-yl)butan-1-one in the form of a colourless oil are obtained in a yield of 100%.

Workup

  1. extractionthe organic compounds are extracted with dichloromethane
  2. customThe organic phase is dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f99ab9da94334c9b82460196afd9b3f5
Source dataset
uspto-grants-2014_11
Patent number
US08877968B2

Reaction notes

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