Potassium Iodide → 3-[3-[4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]propoxy]-benzoic acid ethyl ester fumarate

HRID 1709902Notes

Reaction equation

HRID 1709902 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.[CH2:58]([O:60][C:61](=[O:73])[C:62]1[CH:67]=[CH:66][CH:65]=[C:64]([O:68][CH2:69][CH2:70][CH2:71]Cl)[CH:63]=1)[CH3:59].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].[CH2:58]([O:60][C:61](=[O:73])[C:62]1[CH:67]=[CH:66][CH:65]=[C:64]([O: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]=1)[CH3:59]

Participants

8

Reactant 6

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 444972Fumaric AcidHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 230363354-(Diphenylmethylene)-1-(3-phenoxypropyl)piperidine oxalateHCID 540513773-(3-Chloro-propoxy)-benzoic acid ethyl ester

Product 1

HCID 703732893-[3-[4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidinyl]propoxy]-benzoic acid ethyl ester fumarateYield 67%

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 3.0 g (0.01 mole) of α, α-bis(p-fluorophenyl)-4-piperidinemethanol, 2.4 g (0.01 mole) of 3-(3-chloropropoxy)benzoic acid ethyl ester, 3.7 g (0.035 mole) of anhydrous sodium carbonate and 0.4 g of potassium iodide in 100 ml of dimethylformamide gave a gum as residue. The gum was converted to the fumaric acid salt and the solid was recrystallized from acetonitrile to yield 4.2 g (67%) of title compound as a fluffy,, white solid, mp 123°-131° C.

Workup

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

Sources & evidence

ORD record
ord-a069814467d74366b741b73f7ca7a979
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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