Trifluoroacetic acid → Ethyl 4-ethyl-4-piperidinecarboxylate

HRID 2179754Notes

Reaction equation

HRID 2179754 reaction equation
[CH2:1]([C:3]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:8][CH2:7][N:6](C(OC(C)(C)C)=O)[CH2:5][CH2:4]1)[CH3:2].FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([C:3]1([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:4][CH2:5][NH:6][CH2:7][CH2:8]1)[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 53393415Ethyl 1-Boc-4-ethyl-4-piperidine carboxylate

Product 1

HCID 53393422Ethyl 4-ethyl-4-piperidinecarboxylateYield 95.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-tert-butyl 4-ethyl 4-ethylpiperidine-1,4-dicarboxylate (above step 2, 4.5 g, 12.96 mmol) in 50 ml DCM was cooled to 0° C. After ten minutes trifluoro acetic acid (6.0 g) was added and stirred the reaction at room temperature for about 6 hours. Upon completion of the reaction (monitored by TLC), the reaction mixture was neutralized with saturated NaHCO3 and extracted with DCM, the organic layer was dried over Na2SO4 and concentrated under reduced pressure to furnish the title compound (2.3 g) as a light yellow liquid. 1H NMR (300 MHz, CDCl3): 1.19-1.24 (t, 3H); 1.48-1.58 (m, 2H); 2.14-2.18 (m, 2H); 2.64-2.73 (m, 2H); 2.86 (s, 2H); 3.01-3.07 (m, 4H); 4.10-4.17 (m, 2H); 7.07-7.10 (m, 2H); 7.24-7.30 (m, 3H); ES Mass: 186 (100%), [M+1].

Workup

  1. customthe reaction at room temperature for about 6 hours
  2. customUpon completion of the reaction (monitored by TLC)
  3. extractionextracted with DCM
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-12b0a9a8055343bc98d56cc7369d4b23
Source dataset
uspto-grants-2015_06
Patent number
US09067966B2

Reaction notes

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