Sulfuric Acid → 1-Ethyl-4-(2-fluoro-3-(methylthio)phenyl)-1,2,3,6-tetrahydropyridine

HRID 2358150Notes

Reaction equation

[CH2:1]([N:3]1[CH2:8][CH2:7][C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([S:16][CH3:17])[C:11]=2[F:18])(O)[CH2:5][CH2:4]1)[CH3:2].S(=O)(=O)(O)O.C1(C)C=CC=CC=1>O>[CH2:1]([N:3]1[CH2:4][CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([S:16][CH3:17])[C:11]=2[F:18])[CH2:7][CH2:8]1)[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 1-ethyl-4-[2-fluoro-3-(methylthio)phenyl]piperidin-4-ol (42 g, 156 mmol), sulphuric acid (conc, 8.5 ml) and toluene (200 ml) was heated in a Dean-Stark trap for 20 h. The mixture was cooled to 70° C., water (200 ml) was added and the phases were separated. The aqueous phase was basified with aqueous sodium hydroxide (5 M) and extracted with ethyl acetate (2×50 ml). The combined organic phases was dried (MgSO4) and evaporated to dryness to give the title compound (22.6 g). MS m/z (rel. intensity, 70 eV) 251 (M+, bp), 236 (85), 147 (65), 146 (45), 110 (44).

Workup

temperaturewas heated in a Dean-Stark trap for 20 h
customthe phases were separated
extractionextracted with ethyl acetate (2×50 ml)
dry with materialThe combined organic phases was dried (MgSO4)
customevaporated to dryness

Sources & evidence

ORD record: ord-9aa5049828d74c6fb7ab9cc9692a0319
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763639B2

Reaction notes

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