Lithium Hydroxide → (4-Benzhydryl-piperazin-1-yl)-acetic acid

HRID 1290877Notes

Reaction equation

HRID 1290877 reaction equation
[OH-].[Li+].[CH:3]([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]([O:25]C)=[O:24])[CH2:18][CH2:17]1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1COCC1.O>[CH:3]([N:16]1[CH2:17][CH2:18][N:19]([CH2:22][C:23]([OH:25])=[O:24])[CH2:20][CH2:21]1)([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 789874Methyl 2-(4-benzhydrylpiperazin-1-yl)acetate

Product 1

HCID 4741586(4-Benzhydryl-piperazin-1-yl)-acetic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

An aqueous solution of lithium hydroxide (486 mg, 11.58 mmol, 2 ml water) was added to a solution of (4-benzhydrylpiperazin-1-yl)-acetic acid, methyl ester (2.5 g, 7.72 mmol) in a 5:1 mixture of THF/water (20 ml). The reaction was stirred at room temperature overnight. THF was removed under reduced pressure. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was separated and neutralised to pH7 with 1M HCI. A white gelatinous precipitate of (4-benzhydrylpiperazin-1-yl)-acetic acid was formed which was collected by filtration and dried (1.10 g, 46%).

Workup

  1. customTHF was removed under reduced pressure
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. customThe aqueous layer was separated

Sources & evidence

ORD record
ord-1a7740a2efd247c5af23dbb58c304180
Source dataset
uspto-grants-1998_05
Patent number
US05753671

Reaction notes

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