Hydrochloric Acid → 1-Methyl-4-(2-nitrophenyl)piperidin-4-ol

HRID 637666Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][N:12]1[CH2:17][CH2:16][C:15](=[O:18])[CH2:14][CH2:13]1.Cl>O1CCCC1.CCCCCC>[CH3:11][N:12]1[CH2:17][CH2:16][C:15]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])([OH:18])[CH2:14][CH2:13]1

Participants

Conditions

Temperature: -100 °C

Procedure

To a solution of 19.3 g of 2-bromonitrobenzene in 480 ml of anhydrous tetrahydrofuran cooled to -100° C., 79 ml of 1,6M solution of n-Buli in hexane are dropped under N2. After two hours 10.9 g of 1-methyl-4-piperidone are added and the resulting mixture is stirred eight hours at -100° C. Then 1N hydrochloric acid is added at 0° C. to acidify to pH 2 and the solution is extracted with hexane. The aqueous phase is brought to pH 10 and extracted with ethyl ether. Evaporation of the extracts gives 8.95 g of 1-methyl-4(2-nitrophenyl)-4-hydroxypiperidine, m.p. 166°-167°.

Workup

extractionthe solution is extracted with hexane
extractionextracted with ethyl ether
customEvaporation of the extracts

Sources & evidence

ORD record: ord-67f131508f6c409bb283a677857771ad
Source dataset: uspto-grants-1985_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04558049

Reaction notes

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