Bis(4-fluorophenyl)(piperidin-4-yl)methanol → 1-[3-[4-(1,1-Dimethylethyl)phenoxy]propyl]-alpha,alpha-bis(4-fluorophenyl)-4-piperidinemethanol

HRID 1709883Notes

Reaction equation

HRID 1709883 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[OH:9])=[CH:4][CH:3]=1.Cl[CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([CH3:37])([CH3:36])[CH3:35])=[CH:30][CH:29]=1>[I-].[K+].C(O)(C)C>[CH3:36][C:34]([C:31]1[CH:30]=[CH:29][C:28]([O:27][CH2:26][CH2:25][CH2:24][N:13]2[CH2:12][CH2:11][CH:10]([C:8]([C:16]3[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=3)([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[OH:9])[CH2:15][CH2:14]2)=[CH:33][CH:32]=1)([CH3:35])[CH3:37]

Participants

5

Reactant 2

HCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 129286251-tert-Butyl-4-(3-chloropropoxy)benzene

Product 1

HCID 144071101-[3-[4-(1,1-Dimethylethyl)phenoxy]propyl]-alpha,alpha-bis(4-fluorophenyl)-4-piperidinemethanolYield 41%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 3776IsopropanolSolvent

Procedure

Following the procedure of Example 1, α,α-bis (p-fluorophenyl)-4-piperidinemethanol and 4-(3-chloropropoxy)-(1,1-dimethylethyl)benzene were reacted using potassium iodide catalyst to give with white powder (recrystallizing from isopropyl alcohol) in 41% yield, m.p. 126°-127° C.

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-9f2f695d445a4c198f337d5b86034b09
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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