Trifluoroacetic acid → HCID 15884734, compound

HRID 379521Notes

Reaction equation

HRID 379521 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH3:15])[CH2:10][CH:9]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:23][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH:9]1[CH2:10][CH:11]([O:14][CH3:15])[CH2:12][CH2:13][NH:8]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 15884733HCID 15884733, compound

Product 1

HCID 15884734HCID 15884734, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of N-(tert-butoxycarbonyl)-2-(2-methoxyphenyl)-4-methoxypiperidine (864 mg, 2.67 mmol) in CH2Cl2 at 0° C. was added TFA (9.6 mL) and the resulting solution was stirred at 0-40° C. for 2 hours. TFA was removed in vacuo, and the residue was stirred with 40 mL of 1:1 mixture of CH2Cl2 and 1N NaOH for 20 minutes. The layers were separated and the aqueous layer was extracted with CH2Cl2 (3×15 ml). The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo to afford the title compound as a light brown oil (565 mg). 1H NMR (CDCl3, 400 MHz) δ:3.82 (3H, s, OMe), 3.37 (3H, s, OMe).

Workup

  1. customTFA was removed in vacuo
  2. stirringthe residue was stirred with 40 mL of 1:1 mixture of CH2Cl2 and 1N NaOH for 20 minutes
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (3×15 ml)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24954bae8b9a4b1f8719cb61e622fb67
Source dataset
uspto-grants-2001_10
Patent number
US06300316B1

Reaction notes

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