Potassium Iodide → alpha,alpha-Bis(4-fluorophenyl)-1-[3-(3-methylphenoxy)propyl]-4-piperidinemethanol

HRID 1709930Notes

Reaction equation

HRID 1709930 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.Cl[CH2:59][CH2:60][CH2:61][O:62][C:63]1[CH:68]=[CH:67][CH:66]=[C:65]([CH3:69])[CH:64]=1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>C(O)CCC.CC(O)C>[F:36][C:37]1[CH:42]=[CH:41][C:40]([C:43]([C:51]2[CH:52]=[CH:53][C:54]([F:57])=[CH:55][CH:56]=2)([CH:45]2[CH2:46][CH2:47][N:48]([CH2:59][CH2:60][CH2:61][O:62][C:63]3[CH:68]=[CH:67][CH:66]=[C:65]([CH3:69])[CH:64]=3)[CH2:49][CH2:50]2)[OH:44])=[CH:39][CH:38]=1

Participants

8

Reactant 5

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 127603061-(3-Chloropropoxy)-3-methylbenzeneHCID 230363354-(Diphenylmethylene)-1-(3-phenoxypropyl)piperidine oxalate

Product 1

HCID 23036447alpha,alpha-Bis(4-fluorophenyl)-1-[3-(3-methylphenoxy)propyl]-4-piperidinemethanolYield 62%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 3776IsopropanolSolvent

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(4 -fluorophenyl)]-4-piperidinemethanol, 1.8 g (0.01 mole) of 1-chloro-3-(3-methylphenoxy)propane, 3.7 g (0.035 mole) of anhydrous sodium carbonate and 0.4 g of potassium iodide in 100 ml of 1-butanol gave 2.8 g (62%) of the title compound as a white solid, mp 112.5°-114° C. (2-propanol).

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-79008dadc78649e6ba594ec7ff6a6634
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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