Hydrochloric Acid → HCID 86706860, compound

HRID 717880Notes

Reaction equation

HRID 717880 reaction equation
Cl.[OH:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[N:7]=[C:6]([O:14][CH:15]2[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]2)[CH:5]=1.[OH-].[Na+]>O1CCOCC1>[NH:18]1[CH2:19][CH2:20][CH:15]([O:14][C:6]2[CH:5]=[C:4]([CH2:3][OH:2])[CH:9]=[C:8]([C:10]([F:12])([F:11])[F:13])[N:7]=2)[CH2:16][CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67955066HCID 67955066, compound

Product 1

HCID 86706860HCID 86706860, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4.0 M Hydrogen chloride in dioxane (12 mL, 47 mmol) was added to a solution of tert-butyl 4-{[4-(hydroxymethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy}piperidine-1-carboxylate (0.89 g, 2.4 mmol, from Step 3) in 1,4-dioxane (12 mL) and the reaction was stirred for 3 hours. The reaction was made basic by the addition of 1N NaOH to achieve a pH between 12 and 13. The product was extracted with DCM (6×) and the combined extracts were dried over sodium sulfate, filtered and concentrated to afford product as a light yellow solid (0.50 g, 75%). 1H NMR (300 MHz, CDCl3) δ 7.22 (s, 1H), 6.91 (s, 1H), 5.23 (tt, J=7.9, 3.8 Hz, 1H), 4.74 (s, 2H), 3.26-3.06 (m, 2H), 2.88 (ddd, J=12.3, 8.6, 3.4 Hz, 2H), 2.11 (ddt, J=12.9, 6.7, 3.2 Hz, 2H), 1.92-1.56 (m, 2H). 19F NMR (282 MHz, CDCl3) δ −68.89 (s). LCMS (M+H)+: 277.0.

Workup

  1. extractionThe product was extracted with DCM (6×)
  2. dry with materialthe combined extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f333aadec7f446fa9d186971d5205cff
Source dataset
uspto-grants-2015_11
Patent number
US09193733B2

Reaction notes

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