Trifluoroacetic acid → 4-Methoxy-4-methylpiperidine

HRID 1091711Notes

Reaction equation

HRID 1091711 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1([CH3:23])[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]1>ClCCl>[CH3:8][O:9][C:10]1([CH3:23])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22730047HCID 22730047, compound

Product 1

HCID 203737104-Methoxy-4-methylpiperidineYield 55.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Trifluoroacetic acid (2.54 mL, 32.97 mmol) was added dropwise to tert-butyl 4-methoxy-4-methylpiperidine-1-carboxylate (22) (756 mg, 3.30 mmol) in dichloromethane (10 mL) at 25° C. under an air atmosphere. The resulting solution was stirred at 25° C. for 15 hours. The crude product was purified by ion exchange chromatography, using an SCX column. The desired product was eluted from the column using 7M NH3/MeOH and pure fractions were evaporated to dryness to afford the desired compound as an oil (235 mg, 55.2%); 1H NMR (400.132 MHz, CDCl3) δ 1.15 (3H, s), 1.41-1.49 (2H, m), 1.68-1.74 (2H, m), 2.76 (2H, dt), 2.93 (2H, dt), 3.19 (3H, s), 3.49 (1H, s).

Workup

  1. customThe crude product was purified by ion exchange chromatography
  2. washThe desired product was eluted from the column
  3. customwere evaporated to dryness

Sources & evidence

ORD record
ord-a745cbe8fd6e40b58b2388f0d12c031f
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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