4-chloro-N-methylpiperidine → 2-Fluoro-9-(1-methylpiperidin-4-yl)-9H-thioxanthen-9-ol

HRID 2083764Notes

Reaction equation

HRID 2083764 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1.[Mg].Cl[CH:19]1[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]1>O1CCCC1>[F:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([CH:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)([OH:16])[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 793424-chloro-N-methylpiperidineHCID 6406289H-thioxanthen-9-one, 2-fluoro-HCID 5462224Magnesium

Product 1

HCID 203574862-Fluoro-9-(1-methylpiperidin-4-yl)-9H-thioxanthen-9-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Similarly, 2-fluoro-9-thioxanthone (5.0 g.) is reacted with the Grignard reagent derived from 1.06 g. of magnesium turnings and 5.85 g. of 4-chloro-N-methylpiperidine in tetrahydrofuran as described above to give the corresponding 2-fluoro-9-(1-methyl-4-piperidyl)-thioxanthene-9-ol, m.p. 189°-190° C. The latter is dehydrated by the same procedure to obtain 4-(2-fluoro-9-thioxanthenylidene)-1-methylpiperidine as the maleate salt, m.p. 175°-179° C.

Sources & evidence

ORD record
ord-ede297bbd7c847f9a983da48a7e07aa0
Source dataset
uspto-grants-1978_04
Patent number
US04086350

Reaction notes

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