Oxalic Acid → HCID 86745165, compound

HRID 345489Notes

Reaction equation

HRID 345489 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1.Cl[CH2:24][CH2:25][CH2:26][C:27]([N:29]([CH3:31])[CH3:30])=[O:28].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].[C:40]([OH:45])(=[O:44])[C:41]([OH:43])=[O:42]>CN(C)C=O.O>[C:40]([OH:45])(=[O:44])[C:41]([OH:43])=[O:42].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)([OH:9])[CH:10]2[CH2:11][CH2:12][N:13]([CH2:24][CH2:25][CH2:26][C:27]([N:29]([CH3:31])[CH3:30])=[O:28])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 971Oxalic AcidHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 898524-chloro-N,N-dimethylbutyramideHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanol

Product 1

HCID 86745165HCID 86745165, compoundYield 16%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 6.1 g (0.020 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 3.7 g (0.025 mole) of 4-chloro-N,N-dimethylbutanamide, 8.5 g (0.080 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 100 mL of N,N-dimethylformamide was heated on a steam bath for 16 h. The mixture was poured into 1.5 L of water and extracted thrice with 500 mL portions of ethyl acetate. The ethyl acetate fractions were combined, washed with water and brine, dried (MgSO4), and concentrated under reduced pressure to give a viscous oil. The oil was purified by column chromatography using 300 g of silica gel on a 65 cm×4 cm column, eluted with methanol-methylene chloride (1:15). Fractions containing the desired product were combined and concentrated under reduced pressure to give a viscous oil. The oil was converted to the oxalic acid salt and the solid was recrystallized from 2-propanol/ethyl acetate to yield 1.6 g (16%) of the title compound as a white solid, mp 156°-158° C.

Workup

  1. temperaturewas heated on a steam bath for 16 h
  2. extractionextracted thrice with 500 mL portions of ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. customto give a viscous oil
  7. customThe oil was purified by column chromatography
  8. washeluted with methanol-methylene chloride (1:15)
  9. additionFractions containing the desired product
  10. concentrationconcentrated under reduced pressure
  11. customto give a viscous oil
  12. customthe solid was recrystallized from 2-propanol/ethyl acetate

Sources & evidence

ORD record
ord-91ec7ce62862458a85881eb6c3203a16
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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