Trifluoroacetic acid → (2-Phenyl-piperidin-1-yl)-piperidin-3-yl-methanone

HRID 2362774Notes

Reaction equation

HRID 2362774 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:15])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:22]1([CH:17]2[CH2:18][CH2:19][CH2:20][CH2:21][N:16]2[C:14]([CH:10]2[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[O:15])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 578223103-(2-Phenyl-piperidine-1-carbonyl)-piperidine-1-carboxlic acid tert.-butyl ester

Product 1

HCID 57429185(2-Phenyl-piperidin-1-yl)-piperidin-3-yl-methanoneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1 g 3-(2-phenyl-piperidine-1-carbonyl)-piperidine-1-carboxlic acid tert.-butyl ester in DCM (15 mL) was added 40% trifluoroacetic acid in DCM (6 mL). The mixture was stirred at room temperature for 4-5 h. After completion of the reaction all volatiles were evaporated, water (20 mL) was added and the mixture extracted with (2×25 mL) diethyl ether. The aqueous layer was adjusted with 10% aq. NaOH to pH=12, and extracted with ethyl acetate (2×25 mL). The combined organic layers were dried over sodium sulfate, filtered and evaporated under reduced pressure to yield 0.731 g (95%) of the title compound. (MH+) 273.36.

Workup

  1. customAfter completion of the reaction all volatiles
  2. customwere evaporated
  3. additionwater (20 mL) was added
  4. extractionthe mixture extracted with (2×25 mL) diethyl ether
  5. extractionextracted with ethyl acetate (2×25 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-1e137261b67047bb9df1ff80329f5d22
Source dataset
uspto-grants-2014_04
Patent number
US08691846B2

Reaction notes

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