Trifluoroacetic acid → HCID 63040760, compound

HRID 2364537Notes

Reaction equation

HRID 2364537 reaction equation
C([O:3][CH:4](OCC)[CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][C:8]1=[O:13])C.FC(F)(F)C(O)=O.CCOC(C)=O.[O-][Mn](=O)(=O)=O.[K+]>C(Cl)Cl>[O:13]=[C:8]1[CH2:9][CH2:10][CH2:11][CH2:12][N:7]1[CH2:6][CH2:5][CH:4]=[O:3]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acid2×HCID 8857Ethyl AcetateHCID 516875Potassium PermanganateHCID 63630296HCID 63630296, compound

Product 1

HCID 63040760HCID 63040760, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-[3,3-bis(ethyloxy)propyl]-2-piperidinone (1.52 g, 6.61 mmol) in CH2Cl2 (100 mL) under nitrogen was treated with trifluoroacetic acid (TFA) (1.5 mL, 19.5 mmol) and stirred at ambient temperature for 1 h. After adding an additional 1.5 mL of TFA and monitoring by TLC (EtOAc, KMnO4 stain) for complete consumption of starting materials the reaction mixture was partitioned between CH2Cl2 and 1:1 Sat. NaHCO3:water (150 mL) solution. Extracted the aqueous with CH2Cl2 two additional times before combining the organics, washing them with brine, drying over MgSO4, filtering, and concentrating in vacuo to provide the desired product as a clear oil: 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.78-1.91 (m, 4 H), 2.67 (t, J=6.11 Hz, 2 H), 2.85 (td, J=6.42, 0.91 Hz, 2 H), 3.50 (t, J=5.48 Hz, 2 H), 3.71 (t, J=6.32 Hz, 2 H), 9.53-9.58 (m, 1 H); ES+ MS: 156 (M+H+).

Workup

  1. customfor complete consumption of starting materials the reaction mixture
  2. customwas partitioned between CH2Cl2 and 1:1 Sat. NaHCO3
  3. extractionExtracted the aqueous with CH2Cl2 two additional times
  4. washwashing them with brine
  5. dry with materialdrying over MgSO4
  6. filtrationfiltering
  7. concentrationconcentrating in vacuo

Sources & evidence

ORD record
ord-e0072a387c884ecf965b1942ef6d4bb9
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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