Hydrochloric Acid → HCID 22001230, compound

HRID 325151Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

The title compound was prepared by dissolving the compound of Example 19, 2-(4-hydroxyphenyl)-3-[4-[2-(piperidin-1-yl)ethoxy]benzoyl]-6-hydroxybenzofuran, (3.1 g, 6.8 mmol) in 15 ml of methanol and treating with an excess of 3% hydrochloric acid in methanol. The volume was then reduced by boiling to 15 ml. Warm water (20 ml) was then added and the reaction mixture was further warmed to clarify. The reaction mixture was then filtered, followed by gradual cooling to 0° C., at which temperature the mixture was maintained for about one hour. The crystals, which had precipitated, were collected by filtration and washed with cold water. The pale yellow crystals were dried overnight, resulting in 2.82 g (84%) of the desired title product. mp 213-215° C.

Workup

customThe title compound was prepared
temperaturethe reaction mixture was further warmed to clarify
filtrationThe reaction mixture was then filtered
temperaturewas maintained for about one hour
customThe crystals, which had precipitated
filtrationwere collected by filtration
washwashed with cold water
customThe pale yellow crystals were dried overnight

Sources & evidence

ORD record: ord-b135ca576f3e45c9b3a954aa95c3f8e9
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06221838B1

Reaction notes

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