Tetrahydrofuran → 3-[4-(3,3-Diphenyl-1-propyl)piperazin-1-yl]benzoic acid

HRID 1836807Notes

Reaction equation

[C:1]1([CH:7]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=3)[C:19]([O:21]CC)=[O:20])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O1CCCC1.[OH-].[Na+]>CO>[C:27]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][CH2:9][N:10]2[CH2:11][CH2:12][N:13]([C:16]3[CH:17]=[C:18]([CH:24]=[CH:25][CH:26]=3)[C:19]([OH:21])=[O:20])[CH2:14][CH2:15]2)[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 65 °C

Procedure

The compound (2.00 g) prepared in step (b) was dissolved in a mixed solvent composed of tetrahydrofuran (20 ml) and methanol (10 ml), and a 1 mol/l aqueous sodium hydroxide solution (10 ml) was added to the solution. The mixture was then stirred at 65° C. for one hr. The solvent was removed from the reaction solution by distillation under the reduced pressure. Water (30 ml) was then added to the residue, and the mixture was adjusted to pH 4 by the addition of 1 mol/l hydrochloric acid. The resultant precipitate was collected by filtration, and was then dried to give 1.60 g (85.6%) of 3-[4-(3,3-diphenyl-1-propyl)piperazin-1-yl]benzoic acid.

Workup

customThe solvent was removed from the reaction solution by distillation under the reduced pressure
additionWater (30 ml) was then added to the residue
additionthe mixture was adjusted to pH 4 by the addition of 1 mol/l hydrochloric acid
filtrationThe resultant precipitate was collected by filtration
customwas then dried

Sources & evidence

ORD record: ord-5366cf7781da4955af2d0dd1fa1a4e6f
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06777414B1

Reaction notes

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