Trifluoroacetic acid → HCID 69332283, compound

HRID 350583Notes

Reaction equation

HRID 350583 reaction equation
[F:1][CH:2]1[CH:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][N:4]([CH2:14][CH2:15][N:16](C(OC(C)(C)C)=O)[CH3:17])[CH2:3]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][CH:2]1[CH:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][N:4]([CH2:14][CH2:15][NH:16][CH3:17])[CH2:3]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69332948HCID 69332948, compound

Product 1

HCID 69332283HCID 69332283, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-fluoro-1-[2-(N-tert-butoxycarbonyl-N-methylamino)ethyl]4-piperidinylacetate (236 mg, 0.68 mmol) in CH2Cl2 (10 mL) was added TFA (5 mL) at 0° C. After being stirred at room temperature for 4 hr, the reaction mixture was concentrated. The residue was taken up with sat. NaHCO3 solution and extracted with CHCl3. The extracts were dried over MgSO4 and concentrated to afford ethyl 3-fluoro-1-[2-(N-methylamino)ethyl]4-piperidinylacetate (117 mg, 70%) as a reddish oil. 1H-NMR (CDCl3)δ 1.26 (t, J=7.1 Hz, 3H), 1.58 (m, 1H), 1.70 (m, 1H), 1.99 (m, 1H), 2.14 (m, 1H), 2.27–2.33 (m, 1H), 2.47 (s, 3H), 2.48–2.56 (m, 4H), 2.72 (t, J=6.3 Hz, 2H), 2.90 (m, 1H), 3.16 (m, 1H), 4.14 (q, J=7.1 Hz, 2H), 4.67 (d, J=48.3 Hz, 1H); ESI-MS m/z 247 (M++1)

Workup

  1. concentrationthe reaction mixture was concentrated
  2. extractionextracted with CHCl3
  3. dry with materialThe extracts were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fa88ef674fd74dacabd8cb32d8fa56a9
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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