Oxalic Acid → HCID 86745163, compound

HRID 345478Notes

Reaction equation

HRID 345478 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][CH2:27][C:28]([N:30]([CH3:32])[CH3:31])=[O:29].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].[C:41]([OH:46])(=[O:45])[C:42]([OH:44])=[O:43]>CN(C)C=O.O>[C:41]([OH:46])(=[O:45])[C:42]([OH:44])=[O:43].[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][CH2:27][C:28]([N:30]([CH3:32])[CH3:31])=[O:29])[CH2:14][CH2:15]2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 971Oxalic AcidHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 112521835-chloro-N,N-dimethylpentanamide

Product 1

HCID 86745163HCID 86745163, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7.0 g (0.023 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 4.8 g (0.028 mole) of 5-chloro-N,N-dimethylpentanamide, 9.8 g (0.092 mole) of anhydrous sodium carbonate and 0.3 g (0.008 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 twice with 200 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 250 g of silica gel on a 69 cm×4 cm column, eluted with 10% methanol in methylene chloride. The 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 to yield 6.2 g (52%) of white solid, mp 193°-195° C.

Workup

  1. temperaturewas heated on a steam bath for 16 h
  2. extractionextracted twice with 200 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 10% methanol in methylene chloride
  9. additionThe fractions containing the desired product
  10. concentrationconcentrated under reduced pressure
  11. customto give a viscous oil
  12. customthe solid was recrystallized from 2-propanol

Sources & evidence

ORD record
ord-e733fd7e260a47dca66d3c8a451ce6f9
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

Loading…