Oxalic Acid → HCID 14032489, compound

HRID 1382544Notes

Reaction equation

HRID 1382544 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)=[O:5].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:23][CH2:24][CH2:25][CH:26]([C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1)[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1.[I-].[K+].[C:43]([OH:48])(=[O:47])[C:44]([OH:46])=[O:45]>CCOCC.O.CN(C)C=O>[C:43]([OH:48])(=[O:47])[C:44]([OH:46])=[O:45].[F:33][C:30]1[CH:29]=[CH:28][C:27]([CH:26]([C:34]2[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=2)[CH2:25][CH2:24][CH2:23][N:9]2[CH2:10][CH2:11][CH:6]([C:4](=[O:5])[C:3]3[CH:12]=[CH:13][CH:14]=[CH:15][C:2]=3[F:1])[CH2:7][CH2:8]2)=[CH:32][CH:31]=1

Participants

9

Reactant 5

HCID 971Oxalic AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 768201,1'-(4-Chlorobutylidene)bis(4-fluorobenzene)HCID 13180312(2-Fluoro-phenyl)-piperidin-4-yl-methanone

Product 1

HCID 14032489HCID 14032489, compoundYield 34.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.0 g of 4-(2-fluorobenzoyl)piperidine, 16.9 g of potassium carbonate, 20.8 g of 4-chloro-1,1-bis(4-fluorophenyl)butane, 250 ml of dimethylformamide and a few crystals of potassium iodide was heated at 90° for 8 hrs with stirring. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over anhydrous magnesium sulfate and the solvent removed in vacuo to yield an oil. The oil was dissolved in ether, and oxalic acid was added. Recrystallization of the resultant solid from ethanol gave 10.6 g (34.6%) of 1-[4,4-bis(4-fluorophenyl)-1-butyl]-4-(2-fluorobenzoyl)piperidine oxalate, mp 179°-181° C.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washwas washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent removed in vacuo
  6. customto yield an oil
  7. customRecrystallization of the resultant solid from ethanol

Sources & evidence

ORD record
ord-f5d5355adbf0473c944b3452e24fcc58
Source dataset
uspto-grants-1989_02
Patent number
US04806649

Reaction notes

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