Lithium Hydroxide → 3-[1-(4-Trifluoromethyl-phenyl)-piperidin-4-yl]-propionic acid lithium salt

HRID 511178Notes

Reaction equation

HRID 511178 reaction equation
C[O:2][C:3](=[O:22])[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.[OH-].[Li+:24].O1CCCC1>O.C(#N)C>[Li+:24].[F:20][C:18]([F:19])([F:21])[C:15]1[CH:16]=[CH:17][C:12]([N:9]2[CH2:10][CH2:11][CH:6]([CH2:5][CH2:4][C:3]([O-:22])=[O:2])[CH2:7][CH2:8]2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 585760573-[1-(4-Trifluoromethyl-phenyl)-piperidin-4-yl]-propionic acid methyl ester

Product 1

HCID 585767453-[1-(4-Trifluoromethyl-phenyl)-piperidin-4-yl]-propionic acid lithium saltYield 77.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To 3-[1-(4-trifluoromethyl-phenyl)-piperidin-4-yl]-propionic acid methyl ester (480 mg; 1.52 mmol, prepared in accordance with Example 139) is added lithium hydroxide (72 mg; 3.00 mmol) dissolved in water (6.5 mL). After dilution with tetrahydrofuran (10 mL) the reaction mixture is stirred for 2-4 hours. The mixture is then diluted with acetonitrile until a precipitate is formed. The solid is collected by filtration and dried under high vacuum to deliver the desired compound (364 mg; 1.18 mmol).

Workup

  1. customis formed
  2. filtrationThe solid is collected by filtration
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-2bbac02bdbbc43b794cfb6d901c9daf2
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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