Acetic-formic anhydride → HCID 56987993, compound

HRID 2210696Notes

Reaction equation

HRID 2210696 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][C@H:15]2[CH2:20][CH2:19][CH2:18][NH:17][C@H:16]2[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:29](OC=O)(=[O:31])C>O1CCCC1>[CH:29]([N:17]1[CH2:18][CH2:19][CH2:20][C@H:15]([O:14][CH2:13][C:5]2[CH:4]=[C:3]([C:2]([F:27])([F:1])[F:28])[CH:8]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:6]=2)[C@@H:16]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:31]

Participants

4

Reactant 2

HCID 75269Acetic-formic anhydrideHCID 1328463-((3,5-Bis(trifluoromethyl)phenyl)methyloxy)-2-phenylpiperidine

Product 1

HCID 56987993HCID 56987993, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from (+)-cis-3-((3,5-bis(trifluoromethyl)phenyl)methyloxy)-2-phenyl piperidine prepared from the hydrochloride salt, Example 5)(0.5 g) and formic-acetic anhydride (prepared from 90% formic acid (1.5 ml) and acetic anhydride (3 ml) at 60° C. for 30 minutes) in tetrahydrofuran for 48 h at 23° C. The solvent was evaporated in vacuo and the residue partitioned between diochloromethane and saturated aqueous sodium bicarbonate solution, dried (MgSO4), concentrated in vacuo and chromatographed on silica gel to give the title compound as an oil. Found: C, 57.79; H, 4.39; N, 3.13. Calcd for C21H19NO2F6.0.3(H2O), C, 57.75; H, 4.52; N, 3.21%.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between diochloromethane and saturated aqueous sodium bicarbonate solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customchromatographed on silica gel

Sources & evidence

ORD record
ord-93e071a9633048189861ddee04f71bf3
Source dataset
uspto-grants-1995_10
Patent number
US05459270

Reaction notes

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