Trifluoroacetic acid → HCID 86698251, compound

HRID 530889Notes

Reaction equation

HRID 530889 reaction equation
[N:1]([O-:3])=O.[Na+].C(O)(C(F)(F)F)=O.[F:12][C:13]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:14]=1[O:15][C:16]1([CH2:22][OH:23])[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1.[OH-].[Na+]>O.C(O)(=O)C>[F:12][C:13]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][C:14]=1[O:15][C:16]1([CH2:22][OH:23])[CH2:21][CH2:20][CH2:19][N:18]([N:1]=[O:3])[CH2:17]1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 67983516HCID 67983516, compound

Product 1

HCID 86698251HCID 86698251, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of sodium nitrite (2 mmol, 138 mg) in water (3 mL) was added dropwise to a solution of TFA salt of (3-(2,5-difluorophenoxy)piperidin-3-yl)methanol (1 mmol, 243 mg) in acetic acid (5 mL) and water (2 mL) at room temperature. The reaction mixture was stirred at room temperature for 2 hour, and then heated to 60° C. and stirred for 4 hours. The reaction mixture was cooled to room temperature. Sodium hydroxide aqueous solution was added to adjust the pH of the solution slightly basic. The organics were extracted with EtOAc. The product, (3-(2,5-difluorophenoxy)-1-nitrosopiperidin-3-yl)methanol, was obtained after removal of the solvent.

Workup

  1. temperatureheated to 60° C.
  2. stirringstirred for 4 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionThe organics were extracted with EtOAc

Sources & evidence

ORD record
ord-617a057e36dd4907a0b6f114d23281a0
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

Loading…