Sodium Hydroxide → Lomerizine

HRID 977925

Reaction equation

Cl.Cl.[CH3:3][O:4][C:5]1[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=[CH:29][C:6]=1[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1.[OH-].[Na+]>>[CH3:3][O:4][C:5]1[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=[CH:29][C:6]=1[CH2:7][N:8]1[CH2:9][CH2:10][N:11]([CH:14]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[CH2:12][CH2:13]1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 122125Lomerizine Hydrochloride

Product 1

HCID 3949LomerizineYield 64.2%

Procedure

The 1-(2,3,4-trimethoxybenzyl)-4-[bis(4-fluorophenyl)methyl]piperazine dihydrochloride obtained in Example 4 (20.0 g; 36.9 millimoles) was added to 100 ml of a 20% aqueous solution of sodium hydroxide. The resulting oily product was extracted with 100 ml of ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give 11.1 g of 1-(2,3,4-trimethoxybenzyl)-4-[bis(4-fluorophenyl)methyl]piperazine as an oil.

Workup

extractionThe resulting oily product was extracted with 100 ml of ethyl acetate
dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-bd78c94178324c7cb3f7b4d19a91315c
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04663325

Linked notes

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