Lithium Hydroxide → 3-[4-(4-Chloro-phenyl)-piperazin-1-yl]-2-methyl-propionic acid lithium salt

HRID 511109Notes

Reaction equation

HRID 511109 reaction equation
C[O:2][C:3](=[O:20])[CH:4]([CH3:19])[CH2:5][N: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+:22]>O1CCCC1.O.C(#N)C>[Li+:22].[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([N:9]2[CH2:10][CH2:11][N:6]([CH2:5][CH:4]([CH3:19])[C:3]([O-:20])=[O:2])[CH2:7][CH2:8]2)=[CH:17][CH:16]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 435387603-[4-(4-Chloro-phenyl)-piperazin-1-yl]-2-methyl-propionic acid methyl ester

Product 1

HCID 585764403-[4-(4-Chloro-phenyl)-piperazin-1-yl]-2-methyl-propionic acid lithium saltYield 41.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

3-[4-(4-Chloro-phenyl)-piperazin-1-yl]-2-methyl-propionic acid methyl ester (586 mg; 1.98 mmol, prepared in accordance with Example 59) and lithium hydroxide (60 mg; 2.50 mmol) are suspended in a mixture of tetrahydrofuran (4 mL) and water (1 mL). The resulting mixture is irradiated in a mono-mode microwave oven for 50 minutes at 100° C. The mixture is then diluted with acetonitrile until precipitation occurs. The solid formed is then filtered and dried under high vacuum to afford the desired product (238 mg; 0.83 mmol).

Workup

  1. customThe resulting mixture is irradiated in a mono-mode microwave oven for 50 minutes at 100° C
  2. customThe solid formed
  3. filtrationis then filtered
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-c4c15af77bb347aca88e9fe5a23f365d
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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