2-Trifluoromethyl-xanthen-9-one → 9-(1-Methylpiperidin-4-YL)-2-(trifluoromethyl)-9H-xanthen-9-OL

HRID 2083752Notes

Reaction equation

HRID 2083752 reaction equation
Cl.Cl[CH:3]1[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1.[Mg].[F:11][C:12]([F:29])([F:28])[C:13]1[CH:26]=[CH:25][C:24]2[O:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:27])[C:15]=2[CH:14]=1>O1CCCC1>[CH3:9][N:6]1[CH2:7][CH2:8][CH:3]([C:16]2([OH:27])[C:15]3[CH:14]=[C:13]([C:12]([F:28])([F:29])[F:11])[CH:26]=[CH:25][C:24]=3[O:23][C:22]3[C:17]2=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 27607872-Trifluoromethyl-xanthen-9-oneHCID 30341584-Chloro-1-methylpiperidinium chlorideHCID 5462224Magnesium

Product 1

HCID 203575299-(1-Methylpiperidin-4-YL)-2-(trifluoromethyl)-9H-xanthen-9-OL

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The Grignard reagent from 68 g. (0.4 m.) of 4-chloro-N-methylpiperidine hydrochloride and 9.7 g. (0.4 m.) of magnesium turnings in a total volume of 250 ml. of tetrahydrofuran is obtained following the procedure of Example 3. After all the halide is added, 75.6 g. (0.287 m.) of 2-trifluoromethylxanthone is added portionwise and refluxing/stirring are continued for one hour under nitrogen. The reaction mixture is quenched on ice-water-ammonium chloride to give 9-(1-methyl-4-piperidyl)-2-trifluoromethylxanthene-9-ol, m.p. 179°-183° C.

Workup

  1. customThe reaction mixture is quenched on ice-water-ammonium chloride

Sources & evidence

ORD record
ord-2eac4c89d7b348c9b6e4300edb3a51f4
Source dataset
uspto-grants-1978_04
Patent number
US04086350

Reaction notes

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