Hydrochloric Acid → 4-[4-(3,3-Diphenylprop-2-en-1-yl)piperazin-1-yl]benzoic acid

HRID 1968600Notes

Reaction equation

[C:1]1([C:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:26]=[CH:25][C:19]([C:20]([O:22]CC)=[O:21])=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.[OH-].[Li+].Cl>O1CCCC1.CO.O>[C:27]1([C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:8][CH2:9][N:10]2[CH2:11][CH2:12][N:13]([C:16]3[CH:17]=[CH:18][C:19]([C:20]([OH:22])=[O:21])=[CH:25][CH:26]=3)[CH2:14][CH2:15]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of EXAMPLE 1C (10.00 g, 23.4 mmol) in tetrahydrofuran/methanol (100/50 mL) was added solution of lithium hydroxide monohydrate (2.59 g, 70 mmol) in water (30 mL). The reaction mixture was stirred at 60° C. for 16 hours, then was cooled to room temperature and the organic solvents were concentrated. The white solid residue was dissolved in hot water and then the product was neutralized with HCl (3 equivalents). After cooling to room temperature, the precipitate was filtered off, washed with water and dried in a vacuum oven overnight at 40° C.

Workup

temperaturewas cooled to room temperature
concentrationthe organic solvents were concentrated
dissolutionThe white solid residue was dissolved in hot water
temperatureAfter cooling to room temperature
filtrationthe precipitate was filtered off
washwashed with water
customdried in a vacuum oven overnight at 40° C.

Sources & evidence

ORD record: ord-f868e359823745e8bcd70127cd13138c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426422B2

Reaction notes

Loading…