Potassium Iodide → 1-[3-(4-Ethyl-2-methoxyphenoxy)propyl]-alpha,alpha-bis (4-fluorophenyl)-4-piperidinemethanol

HRID 1709900Notes

Reaction equation

HRID 1709900 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]([C:60]1[CH:70]=[CH:69][C:63]([O:64][CH2:65][CH2:66][CH2:67]Cl)=[C:62]([O:71][CH3:72])[CH:61]=1)[CH3:59].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(O)CCC>[CH2:58]([C:60]1[CH:70]=[CH:69][C:63]([O:64][CH2:65][CH2:66][CH2:67][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)=[C:62]([O:71][CH3:72])[CH:61]=1)[CH3:59]

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 103989133-(4-Ethyl-2-methoxyphenoxy)propyl chlorideHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 230363354-(Diphenylmethylene)-1-(3-phenoxypropyl)piperidine oxalate

Product 1

HCID 230363021-[3-(4-Ethyl-2-methoxyphenoxy)propyl]-alpha,alpha-bis (4-fluorophenyl)-4-piperidinemethanolYield 74.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

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, 2.3 g (0.01 mole) of 3-(4-ethyl-2-methoxyphenoxy)propyl chloride, 5.3 g (0.05 mole) of anhydrous sodium carbonate and 0.3 g of potassium iodide in 100 ml of 1-butanol gave 3.7 g (74%) of title compound as a white solid, mp 118°-120° C.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-b23a47c542cd4c04967b61185daa79a6
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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