4-chloro-N-methylpiperidine → 6-Chloro-2-fluoro-9-(1-methylpiperidin-4-yl)-9H-thioxanthen-9-ol

HRID 2083766Notes

Reaction equation

HRID 2083766 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1.[Mg].[F:10][C:11]1[CH:24]=[CH:23][C:22]2[S:21][C:20]3[C:15](=[CH:16][CH:17]=[C:18]([Cl:25])[CH:19]=3)[C:14](=[O:26])[C:13]=2[CH:12]=1>O1CCCC1>[Cl:25][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[C:14]([CH:2]1[CH2:7][CH2:6][N:5]([CH3:8])[CH2:4][CH2:3]1)([OH:26])[C:13]1[CH:12]=[C:11]([F:10])[CH:24]=[CH:23][C:22]=1[S:21]2

Participants

5

Reactant 3

HCID 793424-chloro-N-methylpiperidineHCID 5462224MagnesiumHCID 706137986-Chloro-2-fluoro-9H-thioxanthen-9-one

Product 1

HCID 203574826-Chloro-2-fluoro-9-(1-methylpiperidin-4-yl)-9H-thioxanthen-9-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The Grignard reagent prepared from 5.9 g. (0.044 mol) of 4-chloro-N-methylpiperidine and 1.1 g. (0.044 mol) of magnesium turnings of tetrahydrofuran is treated with 5.8 g. (0.022 mol) and the above-prepared thioxanthone. The mixture is refluxed for four hours and worked up by the usual procedure to yield 6-chloro-2-fluoro-9-(1-methyl-4-piperidyl)-thioxanthene-9-ol, m.p. 133°-142° C.

Workup

  1. temperatureThe mixture is refluxed for four hours

Sources & evidence

ORD record
ord-d09dbcb27278448d8dc5e8a4ec586e8e
Source dataset
uspto-grants-1978_04
Patent number
US04086350

Reaction notes

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