Ethyl 4-(4-((4'-chlorobiphenyl-2-yl)methyl)piperazin-1-yl)benzoate → 4-[4-(4'-Chlorobiphenyl-2-ylmethyl)piperazin-1-YL]benzoic acid

HRID 1968605Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)=[CH:4][CH:3]=1>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:30][CH:31]=3)[CH2:17][CH2:16]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of EXAMPLE 5B (13.0 g, 29.9 mmol) and LiOH monohydrate (3.78 g, 90.0 mmol) in dioxane (250 mL) and water (100 mL) was heated at 95° C. for 16 hours, concentrated to dryness, treated with water (600 mL), heated to 80° C., and filtered. The filtrate was treated with 1M HCl (90 mL) and the resulting precipitate was collected by filtration and dried to give the title compound.

Workup

concentrationconcentrated to dryness
additiontreated with water (600 mL)
filtrationfiltered
additionThe filtrate was treated with 1M HCl (90 mL)
filtrationthe resulting precipitate was collected by filtration
customdried

Sources & evidence

ORD record: ord-431cc9b7a70a42e28cca0b63d8514040
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426422B2

Reaction notes

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