Hydrochloric Acid → 1-(7-Fluoroquinolin-8-YL)piperidin-4-one

HRID 2241982Notes

Reaction equation

O1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[C:12]([F:21])=[CH:13][CH:14]=[C:15]4[C:20]=3[N:19]=[CH:18][CH:17]=[CH:16]4)[CH2:7][CH2:6]2)[O:4]CC1.Cl.[OH-].[Na+]>O1CCCC1>[F:21][C:12]1[C:11]([N:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH2:7]2)=[C:20]2[C:15]([CH:16]=[CH:17][CH:18]=[N:19]2)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 8-(1.4-dioxa-8-azaspiro[4.5]dec-8-yl)-7-fluoroquinoline (Step 2, 1.73 g) in tetrahydrofuran (50 mL) was added aq. 2N aqueous HCl (10 mL). The resulting mixture was stirred at 50° C. for 3 hours. The reaction mixture was then cooled to room temperature, poured into 2.5 N aqueous NaOH and extracted with ethyl acetate. The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated on a rotary evaporator. The crude product was purified by flash chromatography on silica gel using hexane/ethyl acetate to give 1.17 g of the desired product as a yellow oil; MS (ES) m/z (relative intensity): 245 (M+H)+ (100).

Workup

temperatureThe reaction mixture was then cooled to room temperature
extractionextracted with ethyl acetate
dry with materialThe combined organic layers were dried over anhydrous MgSO4
filtrationfiltered
concentrationconcentrated on a rotary evaporator
customThe crude product was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-dc5fc1d201e44452877f359bbf661964
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07671056B2

Reaction notes

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