Sodium Hydroxide → HCID 11282005, compound

HRID 1840945Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

1.05 g (2.33 mmol) of 2-(2-{4-[1-(2-ethoxy-ethyl)-1H-indol-3-yl]-piperidin-1-yl}-ethoxy)-benzoate was dissolved in 30 ml of ethanol. A solution of 0.19 g (4.66 mmol) of sodium hydroxide in 30 ml of water was added to the previous one and the whole mixture was heated at 60° C. for 2 h. After dilution with water and neutralisation with HCl 6N, the aqueous phase was extracted three times with chloroform. The organic solution was washed with brine, dried with sodium sulphate, filtered and evaporated to dryness. The 4.06 g of crude material was recrystallised in acetonitrile affording 2.54 g (64% of yield)of 2-(2-{4-[1-(2-ethoxy-ethyl)-1H-indol-3-yl]-piperidin-1-yl}-ethoxy)-benzoic acid

Workup

extractionAfter dilution with water and neutralisation with HCl 6N, the aqueous phase was extracted three times with chloroform
washThe organic solution was washed with brine
dry with materialdried with sodium sulphate
filtrationfiltered
customevaporated to dryness
customThe 4.06 g of crude material was recrystallised in acetonitrile affording 2.54 g (64% of yield)of 2-(2-{4-[1-(2-ethoxy-ethyl)-1H-indol-3-yl]-piperidin-1-yl}-ethoxy)-benzoic acid

Sources & evidence

ORD record: ord-8a34fe97b4f5435ab8e4e9386993f8a0
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06683096B2

Reaction notes

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