Potassium Iodide → 4-[4-[4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]butoxy]benzoic acid methyl ester fumarate

HRID 1709911Notes

Reaction equation

HRID 1709911 reaction equation
C(O)(=O)C(O)=O.C1(C(C2C=CC=CC=2)=C2CCN(CCCOC3C=CC=CC=3)CC2)C=CC=CC=1.[F:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]([C:51]2[CH:56]=[CH:55][C:54]([F:57])=[CH:53][CH:52]=2)([CH:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[OH:44])=[CH:39][CH:38]=1.[CH3:58][O:59][C:60](=[O:73])[C:61]1[CH:66]=[CH:65][C:64]([O:67][CH2:68][CH2:69][CH2:70][CH2:71]Cl)=[CH:63][CH:62]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+].[C:82]([OH:89])(=[O:88])/[CH:83]=[CH:84]/[C:85]([OH:87])=[O:86]>CN(C)C=O>[C:82]([OH:89])(=[O:88])/[CH:83]=[CH:84]/[C:85]([OH:87])=[O:86].[CH3:58][O:59][C:60](=[O:73])[C:61]1[CH:66]=[CH:65][C:64]([O:67][CH2:68][CH2:69][CH2:70][CH2:71][N:48]2[CH2:47][CH2:46][CH:45]([C:43]([C:51]3[CH:52]=[CH:53][C:54]([F:57])=[CH:55][CH:56]=3)([C:40]3[CH:41]=[CH:42][C:37]([F:36])=[CH:38][CH:39]=3)[OH:44])[CH2:50][CH2:49]2)=[CH:63][CH:62]=1

Participants

8

Reactant 6

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 444972Fumaric AcidHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 14575308Methyl 4-(4-chlorobutoxy)benzoateHCID 230363354-(Diphenylmethylene)-1-(3-phenoxypropyl)piperidine oxalate

Product 1

HCID 703734324-[4-[4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]butoxy]benzoic acid methyl ester fumarateYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure used to synthesize the compound of Example 1. A mixture of 9.1 g (0.03 mole) of α,α-bis(p-fluorophenyl)-4-piperidinemethanol, 7.3 g (0.03 mole) of 4-(4-chlorobutoxy)benzoic acid methyl ester, 10.6 g (0.1 mole) of anhydrous sodium carbonate and 0.5 g of potassium iodide in 125 ml of dimethylformamide gave a gum as residue. The gum was converted to the fumaric acid salt and the solid was recrystallized from acetonitrile-dimethylformamide to yield 12.2 g (65%) of title compound as a white solid, mp 186°-188° C.

Workup

  1. customThis compound was prepared
  2. customgave a gum as residue
  3. customthe solid was recrystallized from acetonitrile-dimethylformamide

Sources & evidence

ORD record
ord-28ca881b34754dd1a5d6181e1ce5c106
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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