Potassium Iodide → 4-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidineoctanoic acid ethyl ester

HRID 345480Notes

Reaction equation

HRID 345480 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.Br[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][C:31]([O:33][CH2:34][CH3:35])=[O:32].C(=O)([O-])[O-].[Na+].[Na+].[I-].[K+]>CN(C)C=O>[CH2:34]([O:33][C:31](=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][N:13]1[CH2:12][CH2:11][CH:10]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[OH:9])[CH2:15][CH2:14]1)[CH3:35]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 264813Ethyl 8-bromooctanoateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanol

Product 1

HCID 545086394-[Bis(4-fluorophenyl)hydroxymethyl]-1-piperidineoctanoic acid ethyl esterYield 94.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

This compound was prepared according to the procedure used in Example 7. A mixture of 4.6 g (0.015 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 3.8 g (0.015 mole) of ethyl 8-bromooctanoate, 6.4 g (0.061 mole) of anhydrous sodium carbonate and 0.3 g (0.002 mole) of potassium iodide in 50 ml of N,N-dimethylformamide gave 6.7 g of a dark oil. The oil was purified by high pressure liquid chromatography (Waters Associates Prep LC/System 500A; PrepPAK® 500/silica; ethyl acetate-hexane 2:1; flow rate 150 ml/min). The fractions containing the desired product were combined and concentrated under reduced pressure to yield 4.3 g (72%) of the title compound as a viscous, yellow oil.

Workup

  1. customThis compound was prepared

Sources & evidence

ORD record
ord-d2a57d644e9843f8aabc3e1748a4c015
Source dataset
uspto-grants-1991_10
Patent number
US05057524

Reaction notes

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