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

HRID 511181Notes

Reaction equation

HRID 511181 reaction equation
C[O:2][C:3](=[O:19])[CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1.[OH-].[Li+:21].O1CCCC1>O.C(#N)C>[Li+:21].[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([N:9]2[CH2:8][CH2:7][CH:6]([CH2:5][CH2:4][C:3]([O-:19])=[O:2])[CH2:11][CH2:10]2)=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 585760603-[1-(4-Chloro-phenyl)-piperidin-4-yl]-propionic acid methyl ester

Product 1

HCID 585764893-[1-(4-Chloro-phenyl)-piperidin-4-yl]-propionic acid lithium saltYield 90.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To 3-[1-(4-chloro-phenyl)-piperidin-4-yl]-propionic acid methyl ester (345 mg; 1.22 mmol, prepared in accordance with Example 142) 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 product (300 mg; 1.10 mmol).

Workup

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

Sources & evidence

ORD record
ord-325c76c8448a4549a6662fe53e96a43d
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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