Methanol → HCID 22257779, compound

HRID 1835256Notes

Reaction equation

HRID 1835256 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH:13]([CH3:18])[C:14]([O:16]C)=[O:15])[CH2:8][CH2:7]1.O.[OH-].[Li+].CO>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH:13]([CH3:18])[C:14]([OH:16])=[O:15])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 22257738HCID 22257738, compound

Product 1

HCID 22257779HCID 22257779, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 2-[4-(3,4-dichlorobenzyl)piperazin-1-ylmethyl]propionate (470 mg, 1.36 mmol) and lithium hydroxide monohydrate (185 mg, 4.41 mmol) were dissolved in water (5 ml) and methanol (15 ml) and stirred at room temperature. After 21 h, the solvents were removed under reduced pressure. The resulting residue was taken up in a mixture of methylene chloride and water, and the aqueous layer was made acidic (pH 4) with 1M HCl. The layers were separated and the aqueous phase was extracted with several portions of methylene chloride. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure to afford 2-(RS)-[4-(3,4-dichloro-benzyl)piperazin-1-ylmethyl]propionic acid (444 mg) as a pale-yellow foam.

Workup

  1. customthe solvents were removed under reduced pressure
  2. additionThe resulting residue was taken up in a mixture of methylene chloride and water
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with several portions of methylene chloride
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-861f594dbe8a4e40b99c01429c75aef5
Source dataset
uspto-grants-2004_08
Patent number
US06770650B2

Reaction notes

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